Building & Scaling Customer Success
The GTM Newsletter
Back like we never left.
Well, we never really left. But it feels good to be back in the saddle after a week in-between GTM Newsletters.
Absence makes the heart grow fonder? Something like that.
Whatever, I missed y’all. Sue me!
The good news is we have some heat for you this week. Invaluable advice from the front lines of GTM.
We’re covering Building and Scaling Customer Success.
Building & Scaling Customer Success
Acquiring customers is challenging in this market. That makes renewing and retaining current customers even more important. That process starts from the moment of first contact all the way through renewal and beyond.
We’re going to cover it all, and we have the right person to cover it with us - Brooke Simmons.
It’s going to be a slightly different structure than normal. More of an interview-style, fireside chat.
Same golden nuggets of advice, tactical strategies, and stories from the operator chair.
Scott: Let’s start by setting the table. You were the first CS hire at Open Gov, first CS hire at Outreach and a Sr. Director through 5+ years of incredible growth, VP of CS at Spekit, and now consulting a variety of great companies.
Tell us what we’re missing. How did you get started in CS leadership?
Brooke: I'm a reformed management consultant. I fell into consulting out of college because I didn't know what to do. I was incredibly lucky that Deloitte exposed me to so many companies and projects.
I learned that the problems I liked working on were client-facing, and that working in fast-paced software companies was way more fun than traditional industries (airlines, anyone?). I made the jump to start-ups and never looked back.
Scott: Lucky us! That’s a win for start-up world. In your opinion, when should Founders and Start-Ups start thinking about Customer Success?
Brooke: As soon as you realize you have something people want to buy.
Once you're taking money, you're committed to fulfilling a promise of value. Founders often delay critical inputs to customer success because they aren't necessary to ship product.
For example, a lot of companies don't have customer usage data, or they use people to do all the onboarding because the product is hard to use self-service.
I challenge early stage companies to think about scaling customer success from the beginning.
Yes, you can cover gaps with people, but it's far easier to start with a low involvement model and then scale up to higher involvement. Once you have hundreds of customers, that's a harder change to make.
Scott: So what does the early build for Customer Success look like? Who do you hire and what tools do they need?
Brooke: Your customer success motion should be oriented around the business objectives you want your customers to realize, and specific points in the journey where you demonstrate value.
Many companies just focus on the mechanics of onboarding, training, renewals, etc. Those motions make us all feel like we're being productive because we're engaging with customers, but it has nothing to do with the value your customer receives from your product.
Typically the first customer success hire is a total unicorn/hero who will do anything to make a customer successful. That's great for now, but it doesn't scale and it's hard to hire more of those people.
Your first hire should be someone who's great at making scalable programs and resources (1:many training webinars, newsletters, in-app guides, how-to videos).
They have to be super aligned with marketing and your product team. This person should invest in creating a knowledge base or training hub early (something like a Zendesk help site, or Skilljar) versus doing everything 1:1.
Your first hire also needs to create process; look for someone with a process and documentation mindset who can find and create patterns.
📈 How to take action/learnings:
Start early. CS begins as soon as you are delivering a product and value to customers.
Look beyond the mechanics of onboarding. What value do you want to demonstrate? Where in the journey is most important to showcase value? Start there.
Your first hire should be someone who creates processes and scalable programs. 1:many resources, training hub, etc.
Align early CS with marketing, product, and sales.
Scott: Okay we’re set-up and humming along. How do you measure success?
Brooke: Define a user-level metric (like WAU/MAU) that represents real product usage, not just logins.
If you can tie a valuable product interaction to that metric, even better.
For example, at Outreach we had an Admin metric that included critical pieces of the product we wanted the Admin to touch every month. Your early CS team then can focus on getting accounts to that critical WAU/MAU threshold, which is a leading indicator of retention.
Scott: What’s the most common mistake you see early-stage CS teams make?
Brooke: Zero process.
Just a bunch of really motivated, well-intentioned CSMs doing completely manual things to keep customers happy. If you don't have standards, it's hard to A/B test what actually works with customers.
Second mistake I see: way too many accounts per CSM. If you have a complex product with a manual onboarding and zero scalable resources, don't expect a CSM to effectively handle 50+ accounts.
They won't be able to keep up your processes, and you'll see churn on the other side.
Scott: Agreed. Both are easy traps to fall into when you have a scrappy team working hard to make customers happy. The challenge is, that only gets you so far.
What’s the most common piece of advice you’re giving teams you’re advising right now?
Brooke: Really focus on the addressable churn risks this year.
Addressable churn risks are those that you can save with effort: low adoption, delays in onboarding, new point of contact, etc.
Non-addressable churn risks are those you cannot control: company is doing layoffs, your product performance has been subpar, they want you to build new features that aren't in the roadmap.
Your resources are finite. Get realistic about the best place for your team to focus.
Should they continue to spend hours supporting a customer likely to churn regardless? Or, should they focus that time on a customer who could potentially grow, or become a reference?
📈 How to take action/learnings:
Define a user-level metric that makes sense for your business to measure success. Not surface-level logins. Something fundamental to success with your product and focus on that.
Process over hustle. Hustle is great, but it only gets you so far without process. Build lightweight standards and processes to empower your hustlers.
Focus on addressable churn. Resources are finite. Allocate yours to customers where you can impact churn risk.
Scott: Okay, this wouldn’t be the GTM Newsletter if I didn’t ask for a story. Tell us one of the most impactful stories from your career that shaped how you approach CS as an operator.
Brooke: I was working with a large telco company who purchased our product when we were still Series A, but trying to appear Series D.
On my second day on the job, I went out to dinner with their CMO and remember thinking "I've got my work cut out for me." This was a nationwide deployment to 2,000+ sales reps in small offices dispersed everywhere.
We slogged through our standard enterprise deployment, launched the tool, and got zero adoption. By the time the deployment was done, everyone just wanted to stamp the thing as "launched" and get it out.
But, we missed a critical step. The sellers didn't understand the "why change." We never aligned with all the middle managers in the offices that would be the agents of change post-training.
We assumed because it was an executive initiative, that everyone at the office-level would adopt.
📈 I learned a few key things on this deal:
No one really wants to adopt new software. You have to be able to clearly get the "what's in it for me" through to your end users. Screwing up our initial launch made adoption at this account a pain for the next 3 years.
Training without a clear "why change" will fall flat. Managers didn't understand why this was better than what they were currently doing, so they didn't continue to promote the tool after training.
Customer Success is basically a blend of change management and sales, with a dash of technical aptitude thrown in. You're always selling something, even if it's just a behavioral change.
Scott: Brooke, this has been amazing. Any parting words of wisdom for our loyal readers who made it this far?
Brooke: With new business pipeline slowing down across the board, you can't afford to lose customers too.
Even if customers downsell, you still keep that logo and have the opportunity to expand again in the future. Get creative about bringing value to your customer this year and keeping logos where you can.
There you have it, folks! We’ll do more on Customer Success in the future, but hope this got your wheels turning.
Brooke is one of the best. You can check out more from her here.
👀 More for your eyeballs:
Most people Angel Invest without a model or mental framework. Here’s a really interesting framework from Suleman Ali (“Suli”).
👂 More for your eardrums:
Two legends of Social Impact in tech joined the podcast this week: Bryan Breckenridge and Corey Marshall. Bryan and Corey Co-Founded VITAL, and before that pioneered growth and impact strategies at the likes of Salesforce, LinkedIn, Box, Zillow, Snyk and Splunk. We talk social impact in start-ups and how it influences revenue & growth.
🚀 Start-ups to watch:
Huge congrats to the team at BlueCargo on their $11M raise. We’ve all felt the impact of supply chain inefficiencies these past few years. BlueCargo optimizes logistics in port terminals and reduces late fees for drayage trucking companies and shippers.
🔥Hottest GTM job of the week:
Customer Success Manager at LexCheck, more details here.
See more top GTM jobs here.
Thanks for rocking with us until the end.
If you’ve been finding this newsletter valuable, please share it with your friends/colleagues.
Have a great weekend.
Appreciate you.
Barker✌️
loved this:
“Many companies just focus on the mechanics of onboarding, training, renewals, etc. Those motions make us all feel like we're being productive because we're engaging with customers, but it has nothing to do with the value your customer receives from your product.”