Episode Summary
In this insightful conversation, Aaron Woods, an accomplished leader in customer success with experience at companies like LaunchDarkly, Catalyst Software, Datadog, and Fidelity, shared his journey, strategies, and wisdom on building impactful post-sales teams. Aaron’s candid reflections reveal a nuanced understanding of customer success and leadership, offering actionable lessons for professionals in the field.
“Customer Success Isn’t One-Size-Fits-All”
Aaron’s journey in customer success spans nearly a decade, during which he’s consistently tackled challenging roles. Reflecting on his career, Aaron noted:
“There’s no one-size-fits-all approach to customer success. It’s tailored to the product, the maturity of your customer, and the maturity of your company.”
He emphasized the importance of understanding these nuances to build an effective post-sales team that aligns with an organization’s goals and customer needs.
From Sales to Success: A Personal Journey
Aaron’s career began at Fidelity, where he developed the skills that would later define his customer success philosophy.
“Starting on the phones at Fidelity taught me how to deliver a good customer experience. Working with high-net-worth individuals helped me realize that, at the end of the day, it’s just a person on the other end of the line.”
This foundation shaped his ability to connect with customers, even in high-pressure environments.
“Pressure Is a Privilege”
Aaron lives by the mantra made famous by tennis legend Billie Jean King:
“Pressure is a privilege.”
He shared how the intense pace of startups provides a unique opportunity to grow rapidly:
“In startups, you gain five years of experience in just two. It’s a privilege to be in challenging environments where you’re constantly learning and solving problems.”
Mentorship and Leadership: Building Teams That Inspire
Aaron places a strong emphasis on mentorship, both within his teams and across the industry. He reflected on his involvement with Catalyst Coaching Corner:
“I love helping people unpack their career goals. Leadership isn’t the only path—being a top-tier individual contributor can be equally fulfilling.”
As a leader, Aaron believes in empowering his team to take ownership of their roles. He shared:
“I set audacious goals for my team. I want us to be the customer success team that other companies say, ‘We need to hire them.’”
The Future of Customer Success: A Collaborative Approach
Aaron highlighted the evolving role of customer success and its integration into the broader business strategy:
“The best organizations treat customer success as a team sport, not an individual one. It’s about leveraging people across the organization to deliver an exceptional customer experience.”
He’s optimistic about the role of AI in the field, seeing it as a tool to free up time for meaningful human interactions:
“AI can help us focus on what can’t be replicated—building relationships. It’s a supplement, not a replacement, for human interaction.”
Aaron’s insights underscore the importance of a thoughtful, intentional approach to customer success. By fostering meaningful relationships, embracing challenges, and leveraging technology, he exemplifies what it means to drive impactful results in a dynamic field.
“If you want to show up to work every day, feel fulfilled, and keep growing, you have to ask the right questions, build real relationships, and provide value beyond the surface.” – Aaron Woods

Key Takeaways
- Customer success isn’t generic: Tailor your approach based on your product, customer maturity, and company goals.
- Relationships matter most: Treating customers as people—not transactions—builds long-term trust and success.
- Pressure leads to growth: Challenging roles offer unparalleled opportunities to gain experience quickly.
- Embrace mentorship: Leadership isn’t the only path—find what works for you and seek guidance from those ahead of you.
Episode Highlights
0:00 – Welcome & Introduction
Scott introduces Aaron Woods and his extensive experience leading post-sales teams at top SaaS companies.
2:30 – From Sales to Customer Success
Aaron shares how his time at Fidelity shaped his approach to delivering exceptional customer experiences.
5:00 – Breaking Assumptions About Customer Success
Aaron reflects on common misconceptions about customer success roles and why they’re often the most challenging jobs in business.
8:45 – Building Strong Customer Relationships
How understanding that “it’s just a person on the other end of the line” changes the game for customer success.
12:00 – Setting Audacious Goals for Teams
Aaron’s approach to team leadership: setting goals that inspire excellence and differentiate your team in the marketplace.
15:00 – Balancing Goals and KPIs
Why building relationships and understanding customer benchmarks can make your team stand out.
18:00 – Mentorship and Career Development
Aaron discusses his work with Catalyst Coaching Corner and his passion for helping people unpack their career goals.
21:00 – Managing Remote Teams Effectively
Insights on hiring, building culture, and curating team relationships in a remote-first world.
25:00 – The Role of AI in Customer Success
Aaron explores how AI can streamline workflows, surface insights, and allow CSMs to focus on what truly matters: building relationships.
30:00 – Pressure Is a Privilege
How Aaron embraces challenges as opportunities to grow and develop leadership skills.
35:00 – The Future of Customer Success
Aaron’s thoughts on the specialization of customer success roles and the importance of demonstrating business impact.
38:00 – Advice for Early Career Professionals
Aaron’s advice for young professionals: be patient, focus on learning, and trust the process.
all right I’m thrilled to introduce Aaron Woods he is a director of strategic post sales formerly at launch
darkley Catalyst software Daya dog and Fidelity among others um Aaron has over
a decade in customer success and sales and I’m excited to talk to him today so welcome Aon awesome great to be here
Scott thanks so much for having me uh right before our chat uh today Aon and I realized that we’ worked at the same
company dying you know around back in 2015 2016 so we have some mutual friends
uh I personally have a love of being sure so it’s really cool to connect there um so Aaron one of the one of the
things I wanted to just kind of you know just jump into um is I I was looking into your background I think uh reading
about your work history and I think one of the things that kind of comes across a lot over and over is you’re in these
tough challenging roles and so I’m sure people make assumptions about you know
what it’s like to be in your roles and what it’s like to do your job what are some of the things that people have assumed over the years yeah I I think
the key one is that it’s easy um you know I think when I got into customer success almost a decade ago it was kind
of the place that we saw a lot of sellers move to because they didn’t want to have the quota or anything like that
again at that point so um definitely that piece and it’s just the same
process and procedure at every company and you know those are things that I’ve come to be very intimately aware of are
not true um it’s probably the most challenging job in the business and it’s certainly one of the things where it’s
it’s extremely tailored so what the product is where the maturity is of your customer where the maturity of your
company is there’s so many different facets that come into uh making a like a properly good post sales team right I I
100% agree I think um it’s also funny because I think people who are in sales having been in that role myself if you
shift over into a role that’s not necessarily owning revenue or you’re not closing deals uh there’s often that sort
of surprise when it’s like oh wait my compensation changed here a little bit that’s that’s surprising it was a little
jarring when I first made my jump out sales frankly to that but uh it was I
haven’t looked back since it’s been such an awesome awesome transition for me yeah and you’ve and I think it’s really
cool because you you’ve worked on a lot of different very complicated products for really great companies I mean like I
I think I’ve used three or four of the products that you guys have or you personally have worked on over the years
um so I you know I think one one of the things I was really interested in in looking at your work history your
background was um where where do you feel like you I don’t know got the best
training for customer customer success specifically where did that start I
think like the total core of this actually started at Fidelity when I was a broker on the phones there um because
it really it kind of opened up my mind right like it it got me into a position of understanding how to really drive a
good customer experience um and through that end I I ended up working on our high netw desk ended up working on
active Trader desk so I started dealing with really wellbe customer and you know
it’s nerve-wracking at first and and then it kind it slowly transition this is just a person on the other end of the line and I’m actually the professional
in the expert in the room when we’re on this conversation um and that kind of set a really nice Baseline for me to to keep
bring that into my customer success experience and you know I’ve I’ve consistently been working with Fortune
100 companies and you know dealing with VPS and above with those companies and again it’s a person on the other end of
the line or at the other end of the call or at the other end of that handshake they’ve got goals they’ve got aspirations they’ve got things that they
want to accomplish and motivations and like understanding that it’s just a personto person interaction and it’s not
you know this big picture thing uh that can really kind of bog you down and kind of Sidetrack you is such a core thing
that I’m very thankful for the time I spent theity learning those kind of things yeah I think I think that’s a
great point because one one of the problems that I’ve seen is for example our our product we get a lot a lot of
feedback and I’ll get tweets from folks over in Europe that are angry I mean you know frankly all over the world that are
angry about something that not that did not work and then I’ll reach out to them personally and they’re like oh I I
forgot that there’s actually people who work at that and I’m like hey man I I don’t I don’t mind you being frustrated that’s fine but uh that seems to come up
a lot or I I don’t know if you’ve ever been one of those like epic slack battles where you’re going back and forth with a colleague and you’re like
hey maybe we should just like take a call and talk about it I I that’s the like some of the biggest feedback I give
and kind of training any of the folks that have worked for me over the years is like understand when needs to be a
conversation instead of a back and forth right like that’s that’s a skill that I encourage people to develop super early
because it’s so important it changes the absolute trajectory of those relationships and frankly what you can get done and how effectively you can get
it done I I almost wish slack would like gently remind you like hey you’ve been
going back for nine days and you haven’t actually resolved anything you’ve you’ve had 25 slack back and forth maybe a
huddle I don’t know you know yeah exactly that would be that’ actually be great right I’m sure they could figure it out with theyi you found so so like
working with customers um maybe we could talk about both of these but you’ve managed a lot of these great accounts
big small you’ve worked with you know managing a team internally as well so um
making sure that these customers are happy that you know the revenue continues to re uh renew or grow that’s
from my view I think that’s pretty um stressful there’s a lot of pressure there what’s that like and how do you kind of work through you know managing
that yeah you know I I think kind of almost as a bit of a distraction like I try to set really aous goals with my my
team um and in order to do that it’s really like let’s get that Vision pull together let’s get let’s get the right
people onto the conversations uh it’s really establishing that this isn’t a a oneperson show right like it doesn’t
have to rest all on customer success manager shoulders at the end of the day um so really looking at how we can best
leverage people throughout our organization deliver the best experience and coordinate a lot of that um that’s
where I try to focus the team so that they’re not so much feeling like everything’s falling on them and it’s
it’s my it’s only my job to make this happen uh and I try I’ve been fortunate to work at C companies where you know
customer success is not just the customer success team’s problem where people are really thinking about the
long-term play right and like got some exceptional sales uh leaders I partnered
with over the years that have that long-term vision and and start that from the ground floor with these new deals
coming in so it’s train it changes the whole play when we start thinking about it as a team sport instead of a you know
an individual sport at that point for for like the uh I find like the idea of this audacious goal setting maybe maybe
you could kind of clarify because one one thing that it it makes me think of is you know are the goals so insane that
it’s not possible to reach like how do you balance that I yeah probably some clarification on that rather than hard
kpis and that I’m I talk really kind of about from my team’s perspective that I always want to be the customer success
the post sales the technical account manager team that other companies are going I need to hire people from that team okay okay they’re the best in the
business you know really getting to a point where our customers have had such a differentiated experience that we’re
the bar that our customers are setting for other vendors that they’re working with um and like the kind of the
audacious thing I set with team members frequently is with your biggest customer go talk to them who’s the best vendor
that they work with and why and nine CLS out of 10 it’s not going to be you and then but then you have an idea of what
great is to them and that’s stuff that you can build in and hopefully over time you can be the answer to that
question okay I love that um I think I think one I don’t know if this comes up for you but um it comes up a lot for us
where we’re thinking about something new and a lot of the time when we don’t have a benchmark um or or something to
compare ourselves against it can be kind of challenging but I I love the idea of like all right let’s let’s see how
somebody else might approach this and then see if we can live up to that expectation because they’re they’re great we want to be great but maybe
we’re just going to end up with good yeah and that’s perfectly fine too right like what do it say shoot for the stars
line on the moon or whatever it is like at that point as long as you’re delivering a really great experience for the customer that’s what matters most so
um but I think it’s there’s so many different approaches to uh managing customer relationships and their their
life cycles and everything that you know it can’t hurt to ask what’s going well some with another vendor and how can we
what can we beg borrow and steal from that some of that stuff might not apply also right again product and the maturity and all the different elements
and dynamics that we have to consider may not allow us to apply those same kind of approaches maybe we don’t have
enough headcount to do that kind of approach things like that so um it’s just always it’s a way I encourage people I spend a lot of time out in the
the marketplace talking with people in customer success I like to learn what people are doing so it’s my way of kind
of encouraging my Frontline team to go get that same experience without having to get super uncomfortable and reach out to random people throughout the industry
oh that’s nice I love that uh you’re kind of like uh leading by example and taking the bullets before they have to I
guess you most of the time for for some of your team um I
assume you have done mostly remote or some remote what’s been the balance there so uh predominantly remote over
the last five years I had a team in person um when I was at data dog up in Boston before I moved down to New York
so uh but yeah been a lot of remote folks how do you I guess like what have
you seen that been consistent and like wildly different with managing remote team members to build that culture so
that you can lead the way that you want to Leading a remote team is is not for the faint of heart um you know when I
when I joined lunch dark it was my first fully remote job and it took it took some adjustment fortunately I joined
before the pandemic so I got up a year of practice before the rest of us had to jump in two feet on it but um I like
there’s a couple things I really like it from the facet of you know your not constrained to the talent pool that’s
local to you at that point um so I’ve had some really exceptional folks join the team over the years that I wouldn’t
have landed otherwise if I had be in a New York office a Boston office so forth or so on so that’s been really great but
it is it poses a different challenge right you have to spend a lot more uh you have to be a lot more intentional
about curating um the team and the culture um I think one of the key things I do also is I try to hire people from a
lot of different backgrounds it was really helpful with the launch Darkly platform since we sit so centrally in
the whole development cycle so like having people with different backgrounds from across the software development life cycle helps people want to connect
and spend time with each other and Learn and Grow or happen on someone when they’ve got a challenging situation so that’s one way I’ve done it that’s a
little bit more of a back door angle and other than that it’s you know getting you know as we’re having customer ons
sits is you know me getting out there with my reps in the field and spending time where you can have more of those
water cooler chats and like have dinner and chat through stuff and uh but you have to be really intentional about it
when it’s a when it’s a photo remote team for sure yeah because I think otherwise you know you you end up just taking Zoom calls and talking about work
and and you forget that like you need to understand they back to your earlier point that they’re actually a real person they have problems and challenges
in real life too yeah 100 per. um I I’d love to kind of shift a
little bit to you know how you think about mentoring folks that are outside of your team your organization um you
know I think I had read that you had worked with something called Catalyst coaching corner I don’t know if you
started it or worked with it or helped kind of foster it but tell me what it’s like how you know why do you help uh
Mentor folks why is it important to you and what are some of the things that you guys talk about 100% yeah catalst did a
so catalst is a a customer success platform similar to like a game site um emerged with the Tango recently um they
started up this coaching Corner a couple years ago and it was just it was awesome like the first time we did it there was
like 20 people then there was 120 and then you couldn’t get in uh if you hadn’t done it kind of thing so there
were it was a really fun process of going through um and just talking and I talked with everyone from people who
were just trying to grow their IC role and their IC role to people who were trying to get into leadership but um for
me it’s really you know I think I think back to my transition to leadership and
you know a decade ago especially in customer success that was the only path to keep growing as an individual um I
I’ve really spent a lot of time people on my direct teams people just in general in in ic roles kind of examining
that is leadership the path you want or is is being like in the top tier principal CSM kind of the path you want
to go and helping people on pack that and talk that through that’s really kind of what motivates me to do it in general
because you know there days where if I could go back and maybe be a principal CSM maybe i’ take that because you know
leadership certainly comes with its uh its own set of challenges as you’re well this point yeah for sure I was just
thinking like some of some of my favorite times are just sitting next to my you know when I worked at dine in New
Hampshire was like three months out of college just finding people to cold email and then having lunch and going
back to having you know cold emails it’s like the problems that I had in my life were so minimal um but obviously it’s a
totally different set of problems you know I don’t want to diminish that that role but anyway it was it I’d love to sometimes go back but on the other hand
what I get to do every day is quite fun no that’s and I’m in the same boat you know I I have those little Daydreams of
like would my day be easier today if if I was just managing a book at 20 20
customers probably but I really enjoy it and like to me it’s just really interesting to see people progress in
their career um you know kind of coming back to I set that AA goal I want the team to be the team that people want to
come higher from that they want to mimic um in that the the kind of counter
productive thre of that to me is I want people to post people for my team because that means that they’ve done
such a good job job of developing that they’ve made themselves into someone who can be brought to a new company and help
stand something up and build something from scratch and um that’s super rewarding to me it always sucks losing a
person off the team but when they go on to do something greater than they were G to be doing here or uh that’s really
that’s huge to me yeah I I 100% agree I I I actually had two experiences where
one boss was really angry and pissed off when I told him that I was going to leave and then I had another boss who
was like oh that’s amazing that’s like like I think you and I have talked about how that’s what you’d want to do in the future and so are are you you’re
presumably the latter boss you’re not the pissed off boss massively on the ladder side um you know I think it
especially you know unless it’s like going backwards like don’t do that like let’s St yeah yeah yeah that’s that’s
right if if you’re moving your career forward I I will wholeheartedly support that uh in any shape you know I’ve told
people who report to me on a regular basis like if you need if you want to talk about stuff like bigger than this
it’s it’s startup land we do the typical lifespan is you know three to five years in a startup and then you’re going to
move on to something else you’re got to move your career forward typically when you do that let’s have those conversations they don’t need to be
behind closed doors and frankly it helps me if we’re having that conversation earlier I can do a better job of
understanding where my head counts need to be and what I need to do over the next you know six to 12 months to keep the whole team moving in a good
direction at that point too do do you find uh you know just go back a little bit but I’m just thinking about how do
you find find people or how do people find you so that you can help them with
mentorship because I I think sometimes I’ve had this experience with my team where like I have a product manager or a
software engineer who’s like trying to go up to the next level and I’m like hey I can only do so much as the CEO that’s a former sales guy like what kind of
advice do you give people to help them find these mentors yeah places to find
mentors I guess yeah I you know I think a lot of it is just being out there right like I I tell people build your
ecosystem like spend time invest in that ecosystem whether that’s internal to the company you’re at just kind of talking
to other folks and getting different perspectives from different leaders across the business um or outside of
that you know especially if you if you play in devops go talk to people at different uh devops doing that you’re
familiar with and just understand how their process has been and get that Insight it’s there is no simple
straightforward path uh on growing a career right and like I think understanding strengths is the other
thing um I I done we’ve all done those like different strength finders I just recently did the Clifton strength one
and that one actually was like oh wow this thing actually has a lot of meat and it was really neat and I’ve started
suggesting that to people like understand where your strengths are where your easy strengths are that you can go be really great at and figure out
how that can translate into building a career out of it so things like that that I really encourage people to do but
it’s just about getting out there don’t be don’t be don’t be shy you know most most of the people that are out there
that have done well in their career are willing to have conversations about things and kind of share their experience um and you can beg B and
steal what what works for you out of those things and use that to keep growing yourself at that point yeah I
think uh one of my former bosses from Dy uh Kyle York I I would almost describe
him as you know almost like Shameless sometimes like his willingness to talk
about be vulnerable share insights or learnings and then as a result it’s like yeah he he’s able to develop that and
that and that’s only because he put himself out there to start which is pretty interesting uh so with your teams
you know you’re talking these customers so I think one of the things that I’ve experienced is and I think it’s the same
with sales reps customer success uh customer support there’s sort of like this mentality that you could have where
your approach is transactional like where you answer the question and you let them go or you close the deal and
you let them go how do you look at and teach your teams to be not so
transactional I you know I I lean in on the emotional side of this thing pretty heavy right because like what what makes
the job meaningful especially in post sales is where you’re actually able to make a huge impact to the customer
that’s where you get the reward so um really setting that expectation and that Vision you know our job is to be
proactive our job is to add value to these customers um and really help them navigate the way that our tools solve
problems for them um so it’s it’s I usually a lot of it from a framing perspective this is if you want to show
up to work every day feel fulfilled continue to grow you’re going to learn a lot because you’re asking the right questions and you’re you’re having a
much more uh robust and holistic conversation and you’re going to provide a lot more value to that customer um if
you just take what’s on the surface you know you’re you’re going to run up against TR and contraction that you weren’t expecting you’re going to not
feel super fulfilled at the end of the day so uh it really comes back to hiring people that are are motivated
self-starters that to are curious individuals especially in post sales and
I think the same applies to sales frankly if you’re not if you’re not asking questions you’re not learning more about them and you’re not able to
really understand the problems that they’re facing yeah I like the idea of uh you
know asking the right questions I think there’s a there’s a lot of questions that really time can only help you
figure out that they suck um and so being able to ask the right questions and have the right con conversations I
remember there’s a scene in the office with uh with like like Michael and Jan you know Michael is the sort of like
sales manager or the the office manager and then Jan is the regional manager and they’re at lunch and Jan just wants to
go straight to the deal and Michael is like how is your family should we get barbecue ribs and I’ve always looked at
that as like such a great way to go from transactional to personal treat them like a person it seems like you know
again your your kind of response here to me suggests that treat them like real people ask them good questions and
actually understand them develop a relationship yeah the relationship is so key on this too I mean this is the stuff
that you know the best folks that I’ve ever had on my teams over the years have have spent the extra effort you know it
is it’s effort and you have to be intentional about how you build the relationships with the customers and um
when things need to get done if you have the right relationship it’s very easy to get things done it’s very easy to move
the ball forward U but you have to invest up front you don’t get the immediate payout and a lot of that and
again it all comes back to making the job more meaning uh and and something that you want to wake up and do every at that point too
why not have some fun with it make some new friends out of it right yeah that’s right I yeah I also really like that um
so how about like um I feel like you know there’s the personal side of things which we’ve talked a lot about and then
there’s the potential for what’s currently out in the market which is like AI which is sort of almost like a
pretend personal you can kind of get it to mimic or mirror people but it’s like you know it’s like a Bad Robot like
where you’re like that’s clearly a robot it’s this uncanny valley thing like how how are you thinking about AI in your
roles and then also just generally this is uh this is BAS that I’m starting to really get my fingers on because it’s uh
it’s evolving rapidly um but really for me I think it’s a great supplement to
the human interaction right like and and frankly I think the the benefit if it used properly and if the right tools are
developed and and uh put into the toolkit for a CSM or a technical account manager it’s going to allow them to go
focus on the stuff that that can’t be replicated by Ai and uh and do more of that and frankly drive better
relationships and get to a better space with customers and help them see the value there so it’s certainly it’s I
think it’s going to free up a lot more time and ultimately um help companies would differentiate themselves because
they it feels so much more Hands-On even though there’s bits and pieces that are being taken care of but I think there’s
a lot of loow hanging fruit in some of the more mundane day-to-day tasks and like we’re starting to see with data how
do we surface the right data at the right time so that I don’t have to sit there and roll through all 20 accounts
on a weekly basis and check what’s going on what’s not going on where we got flags all that stuff so I’m really
excited for it uh I’ve got a lot more learning to do I think all because it’s coming out really hot and fast at this
point yeah it is it is crazy how I think I saw a video yesterday from open Ai and
I was like they made that with a computer like it it was like a 15minute sequence of three minute Clips
where it was like Lord of the Rings to Call of Duty type videos yeah and it was incred obviously I don’t need necessarily need that as much for work
but I think on the other hand like I talked I I called Google Fiber the other day their customer Sport Line yeah yeah
and it was a robot who talked to me clearly but it was a real man’s voice that’s so crazy I was blown away it was
just like incredible it’s really impressive but I mean like that’s like finding the right places to put it is
really going to be I think what will make people truly stand apart uh and the marketplace especially from a customer
care and experience perspective because you know when we can tell it’s it’s AI it’s also typically when we’re like I’m
the most pissed off right now and I really don’t want to be dealing with this so figure that out is so that’s
that’s like the other super interesting thing is like um I think there’s two parts that I find really interesting is like one unless you unless they’re it’s
so good you’re kind of annoyed and I think the other part is all this AI
continues to come out but really it’s it’s sort of making us more like RoboCop it’s helping us
be more productive and it’s less about taking over our job which is interesting it’s like the promise of the future I
still think we’re gonna be doing a lot of work we’re just gonna be like doing 10x the amount of work I guess it’s
interesting too we actually started see how it goes we started using a tool called Fina um and it ties into slack
and it’s actually it was really neat because it it it uses some AI help decipher is this is what exchange is
happening in a customer facing slack Channel is this a ticket should this be a ticket or is there a dock on our site
that actually helps answer the question and it starts to use all that information and scrape that and and just
quick kind of quickly makes a quicker customer experience gets people to putting in tickets sooner things like
that which is really great you said it was called Athena it’s aena just theena no way cool I’ll check it out um
unsponsored by the way kid yes totally unsponsored I I really enjoyed what we started playing around with was very
tertiary too as far as like what capable of so but it’s cool it’s these are the things that again supplement it right
rather than one of my individuals having to be like hey that’s actually like let’s put a support ticket in for that it would just get that done you know in
very short order and the customer didn’t have to wait around for human on the other end to guide them to that which is
that’s where I can see it being very beneficial yeah totally I I think that’s huge I personally like using YouTube as
my way of finding solutions to a lot of problems and I think knowing that I can go there to end get answer very quickly
or Reddit or whatever or or to you know whatever product that you guys are working on I think is super important um
one of the things that I read that you you wrote about on LinkedIn was this idea that fresher is a privilege um can
you tell me more about that I think it’s a really interesting quote and you know I’d love to hear more about it yeah this
is uh is Billy je king um the tennis player uh that’s her quote so I won’t claim any uh ownership over that but um
it really hit me someone shared it with me and it just was like yeah no I I love that mentality because it’s uh for me
you know I’ve been at smaller startups we’ve been through tons of change it creates a very high pressure environment
um and it’s certainly something that it can be really easy to get bogged out and be like oh this sucks this is a lot of work this is really challenging but for
me U one of my good friends Ray ketti really put it succinctly to me years ago he said you know in startups you get to
get five years worth of experience in the span of two and you can move your career a lot more quickly because you’re
getting these condensed issues that you’re consistently having to solve for so it’s to me personally it’s one of
those things that’s helped me get better and better at uh at making decisions in challenging situations doing so rapidly
taking calculated risks but knowing that I’m not going to hit 100% of the time
there we go all right sorry we’re having Bluetooth issues in the household that hey man things happen I I
wonder if in the AI future that all like the meaningless Bluetooth problems will be fixed but probably not probably not
no I don’t think that ever is going to unfortunately for us all um let’s see so I think you you know
you we talked briefly right before you dropped off about pressure privilege which is great um and how you feel like
it’s an awesome opportunity I think it goes back to your earlier point of like would you love to go back and do your role as like you know the 20 25 year old
or whatever versus the one you have now and sounds like it’s you you appreciate and you like love having this privilege
no 100% 100% it’s just so so much learning in such a compressed period of time frankly that’s just helped me
Elevate myself and learn how to make those tough decisions uh quickly and and
uh and take the risks needed to do that right so keeps helping you learn more and grow more you’re not going to get right 100% of the time either so yeah
for sure yeah absolutely right well I have two more questions for you I think one of the main ones that I’m always interested in hearing from folks is uh
you know you’ve talked about how you think about managing a team how you think you manage your customers or or at
least work with and support them managing them might be you know harder to say we actually do but what what do
you think the future of customer success looks like whether it’s tools working with customers yeah I’d love to hear
more about that this is uh I mean this is a hotly debated topic every moment for sure but um and I think you know I
think the the core of it again to reiterate like there is no one siiz fits-all but I do see uh there’s
obviously there’s a lot more appreciation for what customer success or post sales in general is doing for
especially for SAS products um and really uh I think it’s kind of shifting into
this this moment of you know what does the business need what does the product demand does it demand a lot more
technical Acumen uh and a lot more guidance and handholding from there or is it super self-sufficient and customer
success can take on more of the the the path of of an account management role of
of really helping to drive the the dollars and cents of things and then these businesses were both make a lot of
sense you know the same way that you have an AE and an SE on the pre-sales if it’s technical enough and it’s value
based enough then you could probably benefit from both a CSM and a technical account manager and or bring in
Professional Services so there not really a one siiz fits-all but I think it’s a lot it’s a lot more fluid now and
I think there’s a lot more of an understanding that um instead of it being this this super broad-based like
okay here’s the post sales individual they do everything now it’s starting to see the specialization it’s so important
to really driving much better customer experience much better attention much
growth numbers um kind of all these different things but it’s it’s an investment and that’s where we’re
starting to see a lot of companies kind of come around the corner’ done the es and the flows where 2016 17 18 it was
like you just have customer success because you have it that’s what all software startups now you get into the
the 2020s and it starts to be a lot more of a oh this is a cost center conversation so um the other end of this
too is that that leaders in customer success myself included need to continue to get at really um exemplifying what
the output is and how this is going to help Drive the business and being a lot more clear you know eight years ago when
I was really getting into this deep it was not something that I had to go defend my position as often so I didn’t get as much practice back then as I’m
getting these days frankly yeah I think I think one of the things that uh kind of resonates from from what you said
with me too is that one I think over the last 10 years customer success sort of
is like new it’s it’s a maybe it’s a new title um for an old sort of relationship
thing I think it’s it’s gone through this evolution of like what is it what does it actually do to your point about
there’s so many different roles you could do um and then I also think that I I’m hopeful that people will more and
more appreciate that you can’t just close the deal and leave them alone you always need to have customer success
there to help support each train enable all that kind of good stuff yeah 100% uh
so final final round question for you uh so like if if a young Aaron had walked into the room today or if you were just
talking maybe to you know a neighborhood kid who’s like hey I’m thinking about going to college or or starting my my
career what’s uh what’s important to you what are the things on your mind that you would share yeah I I think one of
the things and I probably realized this midcareer so I I wish I had gone back and told about this a long time ago but
it’s patience um you know like everyone’s moving at a different speed be patient with your learning process
and your growth process um I definitely I think we’ve all been guilty at some point or another of being like ah you
know I can manage better than my manager I can do this or that better than the the person above me and it’s it it’s all
experienced it all comes it’s all quired and it takes time um I’m firm believer that you know you’ll grow in your career
and if you’ve got the right leadership above you then then things will kind of fall into place and just keep keep
pushing down that path um but they’ll move so quickly that you get over the tips of your skis because that’s also a
bad situation at that point right yeah and then eventually you get into the leadership spot and there’s nobody to
complain about by yourself exactly and that’s the more fun part yeah exactly you have to be very introspective at
that rate yeah exactly right well man hey thanks for uh thanks for taking the time to talk with me today and answer
some some great questions with some great answers hey it was a pleasure man thanks for having me all right see yeah

About Our Guest
Aaron Woods, a customer success leader with experience at LaunchDarkly, Catalyst Software, and Datadog, excels in building high-impact teams. He champions mentorship, collaboration, and AI-driven innovation, believing that customer success must be tailored to each business. Guided by the mantra “Pressure is a privilege,” Aaron empowers teams to excel in fast-paced environments.
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