Episode Summary
In this episode of Inside the Workflow, we dive into a conversation with Ben Rosenberg, the Senior Director of Customer Support, Enablement, and Community at ChurnZero. With a background spanning hospitality, finance, and SaaS, Ben brings a wealth of knowledge to leading customer experience teams. His focus on leadership, mentorship, and a human-centered approach has made him a standout in his field. Here’s a closer look at the insights Ben shared during our conversation.
From Hospitality to SaaS: Ben’s Career Journey
Ben’s professional journey began in hospitality and retail before transitioning into financial services at Charles Schwab, where he developed a passion for customer experience.
“I’ve always loved helping people. My time at Schwab helped me see how rewarding it is to solve problems and guide customers through complex issues.”
Today, Ben channels that same passion into his work at ChurnZero, overseeing customer support, enablement, and community-building efforts. His philosophy centers on creating positive experiences and ensuring customers feel supported at every stage.
Leadership Style: Balancing Transparency and Adaptability
Ben’s leadership approach is rooted in flexibility, transparency, and fostering trust within his teams.
“There’s no single best leadership style. The most effective leaders adapt their approach based on the situation.”
He encourages his team to embrace diverse perspectives, valuing agreement and healthy debate.
“I’m big on transparency. Ninety-nine percent of what I know is worth sharing. The more my team understands our decisions, the more aligned we are.”
Ben also emphasizes the importance of maintaining a united front after discussions, ensuring the team moves forward cohesively.
What Energizes Him: People, Problem-Solving, and a Love for Learning
Ben thrives on leadership development and mentorship.
“Helping people grow in their roles and sharing what I’ve learned is one of the most rewarding parts of my job.”
Outside of work, Ben’s hobby of woodworking has taught him valuable lessons about patience and learning from imperfection.
“Woodworking has shown me that you don’t have to be perfect to make progress. It’s okay to make mistakes as long as you learn from them.”
Industry Insights: Challenges and Emerging Trends
Ben is keenly aware of the evolving dynamics in customer support and enablement, particularly in SaaS.
The Shift Toward Digitization
With the rise of automation and AI tools, companies are exploring ways to serve customers more efficiently while maintaining a human touch.
“AI tools are getting better, but for B2B scenarios, they’re not quite there yet. Human-led support might become a competitive advantage in the future.”
Balancing Revenue and Engagement
Ben notes the ongoing debate within customer success about prioritizing revenue versus adoption and engagement.
“The most successful teams strike a balance. Revenue ownership is important, but so is ensuring customers adopt and benefit from the product.”
The Future of Customer Success
Ben sees the industry moving toward greater specialization and leveraging AI to supplement human efforts.
“The next big challenge is figuring out how to serve SMB customers effectively at scale without losing the personal touch.”
He also predicts that tools enabling deeper relationship insights and smarter automation will redefine how customer success managers work.
“Our goal is to use AI to make CSMs’ jobs easier—serving them the information they need so they can focus on building relationships.”
Personal Philosophy: Staying Curious and Customer-Centric
Ben’s advice to aspiring professionals centers on curiosity and customer focus.
“Be curious and learn about every part of the business. Great CSMs succeed because they genuinely care about their customers and are willing to get creative with solutions.”
He encourages leaders to prioritize understanding team challenges and fostering collaboration across departments.
“The best leaders listen and look for ways to help. When you show that you care, people respond.”
Conclusion: A Leader Committed to Growth and Connection
Ben Rosenberg’s journey and insights remind us of the value of adaptability, transparency, and a human-centered approach. Whether he’s mentoring a team member, refining a customer process, or crafting a piece of woodwork, Ben exemplifies the power of continuous learning and a commitment to excellence.
“You have to go into some new experiences with that mindset of: I’m not going to be great at this to start, I’m going to mess it up, but I’m going to try to learn something from each mistake.” – Ben Rosenberg

Key Takeaways
- Leadership Style: How Ben adapts his leadership to different situations and builds trust through transparency.
- What Energizes Him: The joy of mentorship, problem-solving, and even lessons learned from his hobby of woodworking.
- Industry Challenges & Trends: The evolving role of AI, balancing revenue and engagement, and the push for efficient SMB support.
- The Future of Customer Success: Why human-led support might become a competitive advantage and how technology is redefining CSM roles.
- Personal Philosophy: Ben’s advice to aspiring professionals—stay curious, focus on customers, and embrace learning through experience.
Episode Highlights
0:00 – Welcome & Introduction
Scott introduces Ben Rosenberg and his journey from hospitality to SaaS leadership.
3:15 – Leadership in Action
Ben discusses his adaptable leadership style and the importance of transparency and trust.
7:00 – Mentorship and Growth
Why mentorship has been a cornerstone of Ben’s career and how he pays it forward.
10:30 – Energizing Work
Ben shares what motivates him—solving problems, developing leaders, and learning from hobbies like woodworking.
15:00 – Challenges in CX
The push-and-pull of automation and human-led support in the customer experience landscape.
20:00 – Building Remote Team Culture
How ChurnZero fosters collaboration and engagement with remote teams.
25:30 – The Future of Customer Success
Why specialization and AI tools are reshaping customer success and how Ben envisions human-led support evolving as a competitive advantage.
30:00 – Personal Philosophy
Ben’s advice to aspiring professionals: stay curious, embrace learning, and focus on customer-centric solutions.
I’m really excited to welcome Ben Rosenberg from churnzero he is a senior director of customer support enablement
and community so great to have you today Ben and Welcome to our podcast thank you so much happy to be here awesome yeah we
were just talking about Ben’s in Phoenix I’m in uh Utah and it’s just starting to snow it’s 71 degrees for him uh so very
different worlds we’re living in it seems like today um but Ben I you know one of the things I wanted to start off a little bit by chatting about was just
your kind of career you’ve pursued a couple different areas in customer experience and you know it sounds like
you have quite a lot now and I’d love to know at the beginning you know had you been thinking I’d love to work in this
area or what inspired you how’d you end up here that’s a really good question um
and you know I think for me I’m the type of person like I love to host people I
like to help people and just kind of at the core of who I am is that’s a big part of how I operate and how I you know
show my love and gratitude to people as well and um I like many people started my career kind of in the Restaurant
Hospitality did a little bit of retail um and the first uh maybe 10 years or so
of my I guess quote unquote professional career was with the large bank and brokerage Charles Schwab um and that was
really my first like entry into like full-on customer experience type work um
and you know I found that I really enjoyed it um you know just that sort of gratitude of being able to help someone
through an issue or solve a problem and just kind of see the end results of that um something I’ve always had a lot of um
you know passion for um and through my career I would say the the other thing I’m the most passionate about is really
dislike leadership development um it’s one of my favorite parts of my role um it’s what I like spending a lot of time
on with my folks uh you know here at turn zero and otherwise and so I get a lot of uh you know satisfaction out of
taking the things that I’ve seen and done and learned and sharing that across the board too so those are probably the
two top things that come to mind but uh yeah I think it’s just always kind of been who I am do do you feel like um you
know one one of the things so I I grew up in New Jersey but also worked in the Bay Area in sort of the tech world I
tended to find that a lot of the professionals like within my dad’s Network and sort of finance and then also just Tech in the area there was a
lot of this desire to help kind of pay it forward you know people had originally helped you had you found that
early in your career there were folks who were willing to help and kind of either Mentor or train you and maybe
that’s what got you there yeah definitely I’ve had a ton of people like that that I can think of in in my career
and um you know I always sort of joke or tell people like when you know if
someone’s departing a company or um you know I’ll sometimes say us in interviews if it’s like a candidate I really like
but maybe not a great fit for whatever reason um you know like CX especially and CX in the Sass world is a small one
um you know you’ll be surprised where paths cross down line and all that stuff too but yeah mentorship has been a huge
part of my growth I attribute a lot of you know my my ability to kind of lead
different teams and do a lot of what I’ve done in my career to to some of that mentorship and I like to think I do
a pretty good job of trying to pass that pay that forward like you mentioned uh I’ve got a you know pretty pretty large
network of folks that I talk to pretty regularly and try to kind of help navigate uh with them as well and you
know like I mentioned I get a lot of enjoyment out of that personally too so yeah it’s definitely been a huge factor for me as well oh super cool and on the
the leadership side um you know I’m I’m sure leadership is probably same for you
part of it’s experience part of it is practice part of it is maybe observational um so I I found that at
least for me you know U when I work for Facebook I see a lot of great examples of leadership um I’ve read some great
books over the year you know uh there’s one behind me it basically is sort of like the uh the CEO within um and as as
you’ve developed your leadership styles or strategies um have there been maybe
some inputs some themes some areas that really helped you figure out your
approach to leadership yeah it’s interesting like one of the things I try to sort of preach and Coach to my
leaders is like there’s not one good or best leadership style and the most
successful and effective leaders that I’ve um had the pleasure to work with I think are the best at sort of taking the
right style for the situation or for the moment um so when I talk about this with newer leaders like an analogy I use a
lot is just kind of adding arrows to your quiver right there’s a lot of situations you might run into and um you
know being able to sort of use a different approach for for whatever the case might be um has served me really
well and so like a piece of advice that I usually give is like just go talk to other leaders and you know I try to
encourage folks to like talk to leaders they like and have a similar style to but also try to find people where you’re
like o I probably would have never done the thing that this person did um and
like I usually challenge someone like you’ll probably learn something and even if what you take away is like oh yep I
would never do that even though they did like that’s a thing to just kind of keep in the back of your mind um but what I
find more often than not especially with situations like that is you’ll learn something from someone who has a totally
different approach and you know it’ll maybe tweak your perspective a little bit on how to approach a similar
situation so that’s usually one of the main things that I try to focus on um like you I love to read podcast all of
it um you know I just try to soak up as many different thoughts and opinions as I can and yeah I wouldn’t say I have one
overarching theme or style uh I’m really big on transparency um so you know I
think that’s PR pre um Paramount sort of Temple way to think about communication
and building trust so um you know I like to talk about that with my team is like there’s 1% of stuff in my brain that’s
you know sensitive or hre or really can’t be sh shared or whatever but outside of that like the other 99%
there’s no value in me sort of hoarding that in my head and not sharing so I always try to make sure my team’s got
the full picture of what’s going on or why we’re deciding or doing the things that we’re doing and um you know like I
want to be challenged uh you know in the same same way that I would challenge folks on my team too so it just kind of
helps open up some different perspectives and all that good stuff too I I love that I love that you’ve broken
it down into a percentage like you know 1% 99 that’s terrific um I I frequently
feel the same way where if if people un at least they they may maybe they don’t
understand but at least you’ve shared the information to help them hear you know what your goal your motivation is
behind it maybe you can’t convince them maybe they can’t actually understand but at least they know where you’re at what
you’re thinking I think another aspect of that too is like that is healthy right like I
in the past R I’m thinking of a couple experiences of like there’s a right time for that sort of like debate and you
know like hey like push me on this or let’s really like air it out there and um you know like that has oftentimes
change you know outcomes of whatever it is that we’re we’re talking about um yeah I think the thing to be mindful of
there is like once you leave that Zoom or that room or whatever like it’s got to be a united front because if you even
if you don’t agree with where we landed like soon as there’s any you know sort of um like fracture in sort of how we’re
presenting or talking about or whatever then that’s where you really start to lose credibility but yeah I really those have been some of my favorite
conversations in my career um just you know I have a spirited opinion about something somebody’s got a maybe a
different opinion about it and like as long as you do it in a healthy and respectful way like I think those can be really fun and usually come out of it on
the on the other side of for the better I I totally agree especially on the you know disagreement side it’s
especially challenging as a leader who works with other leaders which you know sounds like you do where you need to
make sure you communicate the same message even if three out of five of you are like this is the worst message ever
um I I’d love to know a little bit about you know so it looks like that you know you’re a remote worker like me is that
is that fair to say okay and I’d love to know about you know some of the things that are important to you as a remote
leader in building your team culture like how do you actually do it what’s important to you what are some of your
practices or or approaches to things yeah um you know it’s been interesting I’m sure for many others over the last
few years um turn zero is kind of interesting in the sense that we’ve been remote first um pretty much since
Inception so uh when I joined the organization everyone was like pretty darn good at it and I was still trying
to figure out you know how to build a team and Lead remotely more effectively um you I think some things that we done
that we’ve done a little more tactically uh we do like a daily standup um which is common maybe on like a Dev for
engineering type team but maybe a little less common on the support side so um we do something like that every day it’s
pretty casual it’s like hey what’s going on here’s any big issues for the day anything you’re seeing cases that might
impact anybody else um and it’s honestly been one of the biggest like sort of Team morale and engagement boosts uh
that we’ve had in quite a while it’s it’s just like a sort of low stakes forum for people to just kind of I think
recreate a little bit of like what they might have in office you know and is they’re getting coffee and all that kind
of stuff so so that’s really successful for us um we also do sort of a again a
very like optional come and hang out for a few minutes if you want towards the end of the week where you know a lot of
people just kind of come and hang out and work on cases in like an open Zoom room together or session together and
yeah you know shoot shoot the crap a little bit here and there and all that kind of stuff too so we try to recreate
as much as that as we can and um you know like for me I take a very like
humanistic approach to work where it’s like everyone’s out there they got their own lives going on like you know we’re
we’re deing with SAS support it’s not you know life or death situations in most cases and so we try just try to
have fun and keep it light where we can too and it’s like hard to sort of give like specific advice for but you know we
try to just reframe our work and what we do and you know we take it seriously we want to deliver a great experience we
have you know High goals for expectations and all that stuff too but you got to have a little bit of fun and
you know remember that everyone’s doing what they can with what they got most of the time you know so I I while I do
agree with you on the you know it’s not life or death I do think sometimes
people particularly customers feel like your software bugs problems or issues are absolutely like life or death right
so it could be tough so have you found that either as a leader or as an IC like
is there like a good good way to handle the immense amount of stress that just builds up where you’re like oh my gosh
this guy’s driving me crazy you know because like they’re they’re totally justified and how they feel but like you have to manage it and not freak out at
them right like is there a good way to do it what what have you guys yeah it’s it’s it’s I don’t know if I have a
perfect answer on that you know I’ve had some experience in my career where we deal with like things like payroll or health insurance where it’s like yeah
like an issue can have a really meaningful impact on somebody’s life
right um so you know I think like I’m probably not going to say anything revolutionary here but things like just
kind of taking ownership of the issue like understanding making sure that you know all the different inputs or
whatever to kind of get to a resolution is really important terms of like how do you personally handle or deal with that
or kind of manage the stress like as an I see what I try to tell my folks is
like hopefully you’re at a point where like when you shut down your computer for the day like you shouldn’t be
carrying any of that stress with you outside like there’s always going to be cases to work some of them are going to be harder than others customers are
going to spam the gamut of you know friendly to uh less than friendly or whatever and you know like I kind of
like that sort of diversity of like never really know what my day is going to be like tomorrow even at my level as
a leader right and it’s I think the same thing for the IC so I think it’s a little more about perspective right if you kind of go into it like all right I
might have some gnarly ones today like that’s part of what’s going to make the day go by or you know I really love that
feeling of you know taking a really gnarly complicated issue and getting to a Full Resolution or whatever so those
are some things that have worked for me again in person I just try to like not take it too too seriously obviously I bring a level of professionalism and you
know want to deliver a great experience but um you know I try to I try to separate where I can I I love how you
you know you highlighted that you really never know what you’re going to get that day I think that’s a really important part of work sometimes it’s like if it’s
exactly the same it’s really consistent it it could probably be pretty boring so that’s probably one of the greatest
aspects of of some of the work that you you you do for sure um could you could you talk a little bit about you know for
example let’s you you highlighted really really well how you know you have to obviously set expectations and you have
performance expectations for your team um for managing a team kind of setting that culture i’ I’d love to know like
for us for example I feel like you know helping people just know what their goals are and and then reminding them
and then talking about them seems pretty helpful um H how have you found the right reasonable approach to sort of
like setting those expectations and then helping hold people to account for the those like I don’t know if you’re a
brutal Taskmaster with a whip or you know what you’re like but you know curious um yeah I would say like you
know it’s interesting and I think we might talk a little bit about um you know some teams that are maybe struggling or coming into an environment
like that and I think the first thing for me is always like do they have the tools to be successful and a lot of
times the answer to that question if an or or a team is struggling is like often
times no right like they’ve just been sort of expected to figure a thing out or you know learn how a piece of the
product works or support customers in a certain way and it’s like they don’t even know or they don’t have the things
that they need to be successful so usually that’s where I like to start is just kind of understand and evaluate
like what’s the training and onboarding like what sort of like documentation and resources does the team have how have
they been you know expected to know and understand this info in the past and then okay great now how do we make sure
we get that in front of them at the right time in the right kind of period as they’re learning and once you sort of
check those two boxes then it’s more about like okay now what are the expectations and how do we hold people
kind of accountable to that um one of the things that we struggled with here when I first joined and assume this is
somewhere for a lot of folks out there too like terer is really broad it’s big it’s complicated there’s a lot of
customization there’s a lot of automization in justest a lot of data no two cases are very similar for us here
and so um one of the things we struggled with is like how much should a typical
Frontline agent know about our product or what types of CAS should they be able to handle um so the approach that we’ve
taken here that I think works pretty well for us is we kind of look at it more based on like competencies so we
kind of broken out each of our areas of the product into different competency levels and then the expectation is that
you have a certain certain level of Competency in a certain number of areas of the product so if you grab more
towards one part of the product and it makes a little bit more sense for you than something else then that’s great you can kind of focus there a little bit
more so we tried to give a little bit of flexibility in the sense of trying to
understand that like some folks are a little bit more Technical and they like to be in SQL and JavaScript and do those
types of cases so um we tried to build our growth plan for the team around that
um where I like this structure a lot for us here is it also is kind of a built-in
career progression plan so um we do a lot of like coaching and our year-end process is built around like great you
started the year here where did you add some competency uh where do we still have some opportunity to go and then
sort of our role progression within the support organization um follows a similar paths so in order to be a great
candidate for a senior or a second tier representative you’ve got to have you know a certain level of Competency
that’s a little bit higher in a certain number of areas it’s a little bit more so it really kind of puts all that into
a nice little package for us on the support side um on the enablement side of my job which we haven’t talked too
much about yet um it’s kind of interesting right we uh are doing some 2025 planning right now I’m responsible
for our external enablement so all of our customer training and um sort of enablement on that side and then also
our internal enablement so how do we get the CX or ready for process change or product change or things that we’re
doing internally um and you know one of the things that has been a little bit of a challenge for us on the internal
enablement side is like what are the right metrics for like that um I’ve seen them at almost every SAS company it’s
kind of that like person or small group of people who just kind of are the glue they end up kind of becoming like the
project managers for whatever’s happening and um you know it’s it’s a little bit tougher to like we’re even
trying to plan for what are we going to work on this quarter and like it’ll probably change five times in the in the quarter so um what we’re trying to think
about there is like a little bit more of like how effective is the stuff that we’re delivering rather than um we’re
going to deliver XYZ for the quarter so we tried to kind of rebuild some goals around that um and then we’re trying to
build some goals around like how do we operate and execute on different projects so we’re looking a little bit more in that direction rather than you
know here’s like we’re GNA deliver X automations or we’re GNA you know do
five trainings for the CSM team this month um it’s a little bit more of like what’s the quality are the behaviors
changing because of what we’re doing so we’re looking at some metrics more like that yeah so I I’d love to I think the
metrics part is really interesting because you know I think what one comment uh one of our product managers made the other day was just sort of like
this idea of building products you know for a use case building it for Revenue building it for happiness I think
there’s a bunch of things that are there particular I don’t know outcomes where
you guys are like all right we always want to do X Y and Z maybe within the support world it’s this enablement it’s
it’s that how do you guys think about that yeah I mean on the support side at the metric level I would say we’re not
doing anything super revolutionary there looking at you know things like satisfaction scores response times that
kind of a thing um like I mentioned a lot of our cases are pretty re research
intensive so kind of back to that documentation and knowledge side one of the things that we’re looking at pretty
heavily is like what’s our total like amount of agent working time per case um it was quite high for us here when I
joined it’s not the number one number but I look at that as a really good metric of like have we as a leadership
team done the right thing to make sure that we have have the right people in the right roles that they’re enabled
properly that they have the tools to do their job effectively we do all those things right like that number should be
going down for us and and SE and actually just really quick I I would be super interested to know more about this
total amount of agent working time so like what does that mean exactly and how do you kind of generally keep track of
it yeah so it’s not a perfect number but we use um like within our ticketing system we have a sort of a widget that
runs behind the scenes that looks at like how long was this sort of CAS open and active for them while they’re
working on it there’s some imperfections in exactly how it tracks but you look at it over a large period of time for a
number of cases you’re usually pretty good um so it’s our metric for like how much time are they happen to spend like
researching reading through documentation and pulling up customer information in the product all that good
stuff is is a pretty good metric there and then you know uh if they are getting quicker uncertain case types then we
know that we can draw pretty good correlation that like okay this is a topic they understand have a little bit more competency and all that kind of
stuff so so that’s an important one for us um it ties into the overall customer experience right like how long are they
waiting and what’s our total resolution time for the case and all that kind of stuff is is a little bit of an output of
that too um but yeah that’s that’s been a big one we’ve been focused on the support side for sure cool okay I like
this a lot too because it’s like it is on the agents ultimately but not directly right like if you could put the
absolute best kickass support person in a role but if they don’t have the information they need or the tools
they need or whatever like they’re not going to be able to solve stuff a lot quicker either so I look at this as equally as a reflection of you know
leadership and what we’re doing to support the team as much as it is like the agents individually too yeah and I
think one of the things that you said earlier that it definitely resonated with me was this idea of like uh agents for example not needing to have all of
the context all of the information for every product because like you said your your product is significant and there’s
a lot to know and to do and and rather than be like like frustrated or annoyed at their confidence or quality uh yeah
segmenting it out being specific that certainly helps a lot um so you know one of the things that um I I’m very
interested in I I just I was talking with a friend yesterday actually who uh pully aside but he he’s looking for a
customer success role and we we kind of talked about how customer success depending on which company you talk to
is very different it’s sort of a rapidly evolving of you know industry I’m I’d
love you know from from your perspective I feel like uh what what is customer success how do you
view it and like what’s been changing the most or what do you think the next thing is that’s going to kind of be
significant here yeah yeah I mean it’s really interesting like I have always looked at customer success as a little
bit of a pendulum and it kind of swings back and forth every I don’t know fiveish years or so it feels like as
maybe the the time frame but um you know it’s like a little bit of like how much are they dollars Revenue contract terms
driven versus adoption and engagement and you know product depth and stickiness and um you know in in my
experience like the teams that balance those two things fairly well seem to be the most successful but there’s some
really strong Arguments for both sides of that equation in my mind right like contract negotiations and talking
numbers and getting executive Buy in that is a pretty different skill set from can someone train and adopt and
build long-term you know client success so you know there’s a lot of a lot of interesting opinions on kind of where
that lives and Falls I think what we’re seeing you know we do like a really big CX study every year we publish the
results on our website and those are all really really interesting for me because um what we’re seeing is more companies
are moving towards dollar ownership within CX over the last between between
the two studies um you I think some of that is probably economic realities of you know probably can’t have like a
dedicated management and a CS team right so I think there’s sure some of that over the last year but um you know I
think that is kind of an interesting it’s always an interesting like push and pull and that’s that’s been around forever um you know I think where’re
we’re seeing customers and you know the people in my network and I did some Consulting and stuff before coming to to
turn zero like I think where there’s a lot more serious effort is kind of how do you digitize to some level customer
experience right so you know AI tools are obviously uh expanding in their
capabilities um automation all those types of things but yeah I think the the balance that a lot of companies are
trying to find right now big and small is it’s hard to manage smaller SB customers at scale like it’s an easy
thing to throw a lot of people or bodies at it’s almost impossible to make that economically viable most of the time and
so the types of companies I’ve worked for which are usually you know series C Series D or pre-ipo it’s almost always
the same problem which is is like we built up a pretty big base of all these really small customers we haven’t really
figured out how to service them effectively and economically and like we want to move up Market maybe because that feels easier or we can have bigger
contracts or whatever you know right right right so I think like what’s interesting to me is like the the
barrier to entry to design those types of programs now is um so much lower than
it was even five or three years ago right because um the technology has improved pretty significantly um you
know obviously I’m a little bit biased I was the turn zero customer before I worked here too but like I think our
platform does a great job of like if you need a pretty good all-in-one platform that can do a lot of things really
really well we’re a great option and there are so many other sort of add-on or supplementary things that you can use
with MX organization to really build like a pretty sophisticated you know
automated uh customer engagement program for a relatively small amount of money
right so um so I think that has been really interesting over the last few years obviously I’m sure we’ll talk a little bit more about AI stuff in
general I think that’ll be really interesting to see where things head but um one of my hypothesis over the next
five or 10 years is like I think human Le support will be a little bit more of
like a competitive Advantage choice for customers rather than a you know must have necessity um I don’t know where
that’s going to shake out I think it’ll be really interesting to kind of watch and see where that heads but uh yeah I think that that’ll be uh that’ll be
interesting to watch for sure I I 100% agree with the human Le uh or you know
human assisted with AI yeah it seems like there’s a lot of this sentiment around how can I replace my customer
support team how do I replace my customer success and I I anytime I I am
interacting with a company that seems to do this whether I call their support like I give you an example I have Google
Fiber I called their support they had a great customer support AI agent that
like spoke with a voice and it was really incredible but it just I don’t
know it was it took me it was a little complicated and similarly when I I go to a website and uh you know it’s just a
chatbot only and the chat bot’s not great uh you know we’re we’re guilty of this sometimes too but like it’s so I
don’t know energizing when you finally get to somebody after having that tough but it makes me wonder if if uh we’re
going to make the problem really bad before it starts to get better yeah I do think there’s going to be some of that I
mean I’ve had like a poorly implemented AI solution is just so so painful um
it’s one of the things we’ve struggled a little bit here internally like are we going to deploy something like that for
our team I have yet to find something that like works well enough for B2B
applications where it’s like I feel great about putting this in front of a customer there’s some pretty good tools out there but you know my sense has
always been that like these are great for B Toc kind of things where it’s a little more repeatable you know like
where’s my order what’s the delivery status I need to make a change to a thing that I can just go grab a piece of
information from another system great that’s getting better the conversation side of it’s getting pretty good like all that stuff seems to be there but you
know like to answer most of the questions that our customers have you need to have like what’s the context
somehow they’re set up how did they configure this part of the thing where are we getting their data from right it’s like yeah I can pull some of those
inputs in but the the the sort of connectivity of all that stuff just isn’t quite there yet to a point point
where it’s like yeah this is going to deflect you know half of our cases or anything we just haven’t found anything out there in the market like that um and
you know to your point it’s like do we even want to do that right like is that how we want to be known for sort of
delivering an experience for our customers who are you know largely doing the same type of work that we are which
is kind of an interesting Dynamic for for us specifically but um so yeah I think that’ll be really interesting and
um yeah it it it’s cool and like I love technology I’m a huge n for all that
kind of stuff and it’s been really cool to kind of see it as a as an operator and administrator of a lot of these types of tools but um yeah I think
there’s still quite a bit of room to go for them but they the rate at which things are improving is you know pretty
pretty stunning to see in a in a really cool way yeah I I 100% agree how how quickly it’s changing um I frequently
have videos that my sister sends me on you know social tools Instagram or whatever and I’m like I I don’t know if
that was real or not like that’s crazy um so so so for how about how about for you guys so like maybe specifically from
a turn zero product perspective um when you guys are thinking about what it looks like to make your csms just
incredibly effective um what are you finding that they’re excited about that you guys are thinking about either
building or you plan to build or you’ve already stated you’re going to build I don’t want to you know get into any secret SAU stuff uh yeah no totally uh
we uh are actually doing um we do sort of a one of the things I love about our
chief product officer she does like a presentation every year for customers that’s like our full road map so she
goes into pretty good amount detail about like what we’re working on all that good stuff so I don’t steal any Thunder from that which is upcoming here
in a couple weeks but I would say like we’re largely ey focused uh for the year it’s a big component of our our product
road map um some of the themes that we’re kind of thinking about are um looking at things like overall customer
relationship and sentiment right like the tools are getting really good in terms of analyzing communication and
back forth so we’re doing some really interesting things with that um one of the really cool features we’re um doing
some internal testing on right now so I’m geeking out over it is looking at like the relationships that you have
with different people uh in sort of contacts at different points of the company so got some cool stuff happening
there um we have a lot of AI stuff integrated into our platform already so we have a lot of enhancements coming in
that regard to but you really it’s like review AI um in terms of how CSM might
use it as like a little bit of like a supplementary tool right like how can we make their job a little bit easier or
faster or serve them the information that they need um so we’re working on lot stuff like that for sure um but yeah
internally um you know it’s one of the where as like customer we we use like quite heavily actually both sides of my
role um so for the support team you like I mentioned a lot of our cases are really complex we do a lot of like
asynchronous video so yeah rather than like here’s 10 screenshots we’ll record a video in the customer instance and
kind of walk them through whatever’s going on um one of our goals for this year on the internal enablement side we
got a lot of feedback this year that like hey like an hourlong meeting or training session it’s you know hard to
pay attention to or hard to find time for whatever great we’re going to meet you where you want to be met so uh we’re
starting to do a lot more training through uh through video as well where it’s like watch it at your leisure uh
one of our little tricks is we throw a little like nonse Factor nugget in there and we like like uh we ask like hey did
you see the thing or uh the one we did in the last one was like what was Ben’s favorite color I said my favorite color
was orange so we stuff like that is just a way to like kind of you know keep things fun and light and maybe a little bit more engaging too um but yeah that’s
been a big big part of uh how we’ve we’ve deployed site internally too and we find that works pretty well as well
oh cool okay yeah how about on the uh you know I don’t know if this is something that you own or you work in
but sort of un likee obviously there’s like the Frontline support helping create training documentation but like
when it comes to maybe like a support center or your help center whatever you want to call it um do you guys find that
like people watch videos for your product or do they prefer to read I I
mean I’m more just generally curious what you guys find yeah that’s a good question so uh so yes I am responsible for our like customer Academy which is
like training courses that’s a lot of video driven content um the knowledge base we kind of co-own with the product
team here um I would say one of the we get this feedback all the time on the
academy side which is likei want more Hands-On type content um so we’re we
have a few courses that we’re experimenting that use this kind of a tool where it puts customers into like basically a dummy account environment
and it’s a little bit of like a click along kind of experience which has been cool uh but we it’s funny we were
talking about this last week we’re we’re thinking about some like different modalities so uh you know we’re we
originally were a little more focused on video last year um this year I think it’ll be a little bit more Hands-On
we’re also talking about audio formats as maybe an interesting like let’s experiment with that uh a little bit um
so we’re going to play around with that there too uh but yeah I’d say more often than not we get a lot of either video or
Hands-On are the two things that our customers are looking for I think it totally makes sense um I you know at
least for me whenever I have to fix anything my wife frequently makes fun of me but I’m like instantly I go to
YouTube right sure and and uh the other thing too is I listen to a lot of
podcasts because I’m driving around I’ve got four kids so having it and I love I love the idea of the audio mod modality
um so anyway I’d love to hear more about that when when you’re done with it um let’s see um so you you’ve had a lot of
great experience around sort of building teams helping uh build you know this sort of
products help your customers understand them and and you’ve had I think well from from today at least some really
cool insights on the the the the AI aspects of implementation in your your company um what what do you think like
if you were to start over if if you were to build your own company you or or start a company from from scratch what
what are what’s your like one thing you’d want to prioritize above everything else so like let’s let’s assume that you had a product the
product is great yeah people are happy about it what would you do what would you care about uh yeah I mean it’s a
really interesting question I think like uh I would answer that maybe in a slightly different way which is like
think where things go wrong is you try to be like too many things to too many different people right like it’s really
sexy and attractive to try to say like oh could we you know add a way a bigger
addressable Market or a larger potential user base and um that can work and
that’s important you do have to grow right like there are realities of growing a business that may necessitate some of those things but I would say
like just kind of being true to who you are and what you want to be is really important to me um and then like you
know I think maybe a little biased because of my role in the post sale organization
but you know I think listening to customers is really important right like I’m maybe a little unique as a support
leader I want sales selling ahead of where the product is a little bit right and like kind of pushing the product
from that perspective because reality is like that’s where customers want to go so like let’s try to get them there so
it doesn’t really bother me when it’s like oh sales told them we could do X and we we can do x minus one right now
how do we fill the Gap um you know I think that is really important um I like to think of like support specifically as
kind of the central nervous system for the organization like we kind of have the you know pain receptors and the joy
receptors and um we can kind of relay that back to the rest of the business so
I view that as a really important part of what we do and I think keeping that as part of your company ethos is is really important and you know like have
a good product right like it’s funny we they talk about this a lot in CX where it’s like oh like this customer turned
because of whatever and it’s like a lot of times like maybe wasn’t a good product or wasn’t a good fit or they
weren’t using it it’s like there’s nothing that CSM is going to do in some of those cases too so yeah obviously having good product is uh is important
there too oh yeah absolutely I I feel like every time I I and this is more you
know from I guess trying to be a better customer success manager myself but
every time I look at a customer cancellation a turn reason I’m like I’m sort of like Dr house if you’ve seen
that show he just tends to not believe the reason yeah and I’m like my product
must suck I must have done something so badly um and then I and then I email
them and I’m like hey I hear you know I understand you said this could you tell me a little bit more and and actually I offer people a lot of the time I’m like
I’ll give you a $50 gift card if you just like take 10 minutes with me and talk with me about it and I feel like that helps a lot um I I love your point
though around um the customer nervous system being you know basically the the feedback that’s coming from using the
product and then also just talking the customers I talked with uh a CEO just last week and he said the the way that
he basically came up with the idea of his business was like he said first he thought about the Tam and then second he
started talking to people and as as he talked to potential customers of some of his ideas they really helped guide him
where he could go and then basically he it was funny because he basically was
saying I am not the smartest man I’m not like a genius by any means or anything like that we just talk to customers and
they helped us build something awesome which I think is is really consistent um let’s see so I I think uh you know
completely moving away from some of the uh the business stuff the work stuff um
you have this love this personal love woodworking being outside and I’d love
to know a little bit about the woodworking because I love I’m a bad worker woodworker myself but you know
where are you on the the scale are you making like incredible stuff are you just goofing around what’s it like uh
I’m definitely towards the bad side of of that spure it was it was my sort of quarantine
hobby pickup um so I’ve been doing it for you know three four years at this point um it’s interesting we had talked
about maybe like how does this sort of influence my my leadership or or work style so I’ve been pondering this
question uh for quite a while because it’s really quite interesting to me um I
think like you know it’s funny I did I think a common woodworking thing which is like oh cool I want to get into this
I’m going to go buy like all of the tools right I’m going to go buy like a nice table saw or whatever um and then
it’s like cool I have this pretty nice piece of equipment I have absolutely no idea what I’m doing or like anything
like that like I’m just gonna try to build a box uh so uh yeah know like I think one of the things I would take
away from that as I as I think about how it’s maybe influenced my my mindset towards work is like there’s a lot to be
said for just kind of experience and learning through doing and not expecting Perfection UPF front like I think about
some of the first things I tried to make uh you know out of wood were just you know like laughably laughably bad um but
like I learned something right like oh if I hold it like this like it’s not going to be very straight um and you
know like if I don’t make sure my measurements are accurate on either side like it’s never going to look good
regardless of what I try to do so I think it’s a little bit of just kind of like you have to go into some new
experiences with that mindset of like I’m not going to be great at this to start I’m going to mess it up um but I’m
going to probably try to learn something from each of those mistakes um and you I think like the other thing I take away
from that is like you can be your own worst critic especially in woodworking like I will notice any imperfection or
you know H gosh if I could like reglue this up in a certain way like and then like you know my wife or whoever look is
like are you kidding me like I would have never noticed that in a hundred years or whatever so so I think that’s
the other side of it too is like you got to be able to live with your imperfections and um you know don’t let
perfect you the enemy of good um I like to joke with uh someone in my enablement team about this a lot here it’s like
doesn’t all have to be Pixel Perfect Right like let’s get it out there let’s get some feedback let’s understand what works and let’s take the things that
work and drop the things that don’t I try to take that same approach on the on the woodworking side as as I do on the work side I I love it I think the you
know perfect is the enemy of good just it’s like chef’s kiss great great um so
fi final question for you this is sort of going back to the beginning when you talked about providing guidance to those
who are looking for for roles you know if you think about like yourself or somebody that’s younger they’re aspiring
to find a role in customer experience what would your advice be what kind of advice would you share yeah I can speak
to what has worked well for me and that’s just be curious like um you know I think uh one of the companies I had a
lot of sort of vertical growth in I would attribute to like I heard something was not going well or like
someone needed help somewhere I’m like cool like can I help like tell me where you’re stuck let me learn about this
part of the business or this other team or this process um so that has been a tip that I like to share is just be
curious try to learn as much as you can about the business and the product and every other’s team or other teams in the
in the business um from a leadership perspective one of the things I like to do especially if I’m like new to a
company is like ask the other leaders like hey what are you struggling with in your team like is there anything my team
is doing to make your your day-to-day worse or is there anything I can maybe help with that um you know you’re kind
of stuck on or whatever and I think like just having that understanding like what everyone is facing or what challenges
they’re trying to solve for um I think you’ll find a lot of times that like oh like I might actually be able to help on
this or you know we uh have an interesting thing like that here between support and implementation teams it’s
like oh like we could actually probably handle this a little differently in support and maybe that takes some time off off of your guys’ plate so um I
think those are things that have been helpful for me um you know I think like the people who have the most success in
customer success more generally are just customer centrick like it sounds really stupid and like straightforward but like
that’s it just you know care about your people um try to do what you can like try to get creative with Solutions and
um you know I think a a really strong CSM can look and act and perform in a
lot of different ways which I think is one of the most cool things about that type of role like yeah you could be great at the product and be you know
like a super nerdy whiz at you know helping every single customer fix all of their nitty-gritty things and be really
successful as CSM that way or you could be like a full-on relationship person who can you know get anyone open and
talking for an hour and you know never talk about the product at all and be really successful that way too so it’s
one of the things I really enjoy about this CX World more generally is you can find success no matter who you are
awesome well I love those great final closing thoughts Ben and uh just you know just to wrap up I just wanted again say thank you for joining us today and
sharing these great thoughts cool thanks always pleasure and uh yeah enjoy being on all right

About Our Guest
Ben Rosenberg, Senior Director at ChurnZero, excels in customer support, enablement, and community. With a background in hospitality, finance, and SaaS, he champions transparency, adaptability, and human-centered leadership. Passionate about mentorship and AI-driven innovation, Ben believes in balancing automation with genuine customer relationships to drive success.
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