How Business Strategies Differ At Early Stage vs. Late Stage Startups, and How it Impacts The Customer Success Role

We’ve all been there: you hate your boss, and you’ve decided it's time to move on. You pour your frustration into interviewing, but your interview strategy is all over the place. Different company stages, different types of products, different team structures. How do you know what’s the right fit?

To answer this question, I spoke to Karla Abea. Karla is an Enterprise CSM at Twilio Segment and in her 7.5 years in customer success, she's worked for unicorns like Amplitude and AppsFlyer.  She shared examples of how to evaluate an employer’s strategy, product-market fit, and red flags to lookout for. 

Aisha: How do you tell the difference between a good product and a bad product, and what kind of impact does that have on a company?

Karla: I think a good way to approach this question is to talk about signals of a company set up to build a good product. In earlier stages it’s definitely a good sign for the Product team to be hungry to learn how the customer is using the product, interviewing them, perhaps even establishing a formal Customer Advisory program. A siloed Product team that isn’t asking questions can be a red flag. 

To vet for this specifically, I’d ask what the processes are that inform product direction, and the role that the CSM plays. I’d also ask what informs Customer Success goals. I find that some of the best mid-stage startups who have figured out product market fit and defined their vision, have also defined their strategy and are recruiting various teams across the org to support those strategies. While I was at Amplitude, for example, they defined their North Star Metric. It was a metric by which Amplitude measured that customers were getting value from their product, align on the definition of "value," and help them steer clear from vanity metrics. If a customer was increasingly getting value from Amplitude, their measure of the North Star Metric would increase. So we as CSMs could also measure the impact of our work based on this value, and we were aligned on what "good" looked like. So goals should be informed by a clear vision and strategy.

Another approach is to take a look at what’s being written about them by folks like Gartner and on sites like G2Crowd, as well as on app marketplaces like the Hubspot and Salesforce App Marketplace. Listen for if the same issues are coming up year after year, or if the product team seems to be responsive to feedback. Look for the reviews written by power-uses and pay attention to their feedback.

Aisha: You’ve worked at 6-person startups, 60-person scale-ups, and a 6000 person unicorn: how would you contrast them, and what type of person will succeed in each? 

Karla:

Early-Stage (6-Person) 

At a 6 person company, the teams are leaner with everyone wearing a lot of hats. You’re part of creating lots of processes, from how to support customers, to how to triage bugs/unexpected behavior. You’re learning a lot about the customer's pains not just directly related to the product but sort of in the periphery of the product as well. So, as a CSM, you end up playing Product Manager, Product Marketing Manager and Solutions Architect. 

Another benefit of an early-stage startup is you have tremendous visibility: you’re at the forefront of learning from the customer and helping leadership translate that into the next iteration of the product. You get to see the product built first-hand. 

Are you comfortable with ambiguity? At a startup, you’ll be developing processes as you go, doing things that don’t scale. And shifting directions. Are you okay with this?

You also must be comfortable working independently with minimal guidance. Ask yourself: is being scrappy your strength? Or do you hate hitting a wall? 

The most important part is to be comfortable with the company not going anywhere, while keeping your own interests in mind. I once worked for a company that fired 2 rounds of sales teams, after which our CEO became the interim sales guy. "Eventually I became dissatisfied with the lack of growth. That’s when I knew it was time to call it quits. 

Growth-Stage (60-Person) 

Culture

A 60 person company is different. Rather than building processes, you’re plugging into existing processes, but you still have some authority to improve them. New roles get created and new offices may be established, so it’s an exciting time. 

There are challenges, too.  In one case, as we started preparing for an IPO, we started bringing in bigger-hitters. That was exciting, but as the culture started to shift, it was rough for the more tenured folks. These types of cultural shifts are inevitable, and can be a huge opportunity for the team members who want to grow along this new phase of the company -- not everyone does, and that's okay.

Discovery

At the growth-stage, the leadership team should understand where the product fits in the market, the pain the product addresses. They should have a vision for where they want to take the product. As a CSM at this stage, you’re still educating the customer a lot on your product and how it’s solving their pains, or how they have pains they didn’t even realize could be alleviated by something. This is especially true for category creators. People don't recognize they have a pain, or what the pain represents. Customers need education on their pain. The CSMs who succeed at this stage are excellent at discovery, and attaching pain points to a product. So, if BANT is your strength, a 60 person company may be a good fit.

Strategy

At this stage, scale-ups also start to work toward moving upmarket from SMB to Mid-Market to Enterprise. So as a CSM, if that’s of interest to you, then it’s a great opportunity to contribute to and operationalize how the company can support bigger and more strategic customers. 

Late Stage (6000-Person) 

A 6000 person company is likely to post-IPO. Processes are much more formalized, and the start up mentality may be waning. The company is now a serious player in the industry and wants to recruit the skills that reinforces this status. You may still be cementing your move upmarket, so growing those lands becomes a much bigger part of the growth strategy. 

Unlike early stage startups, you’re not wearing many hats and your role is becoming more specialized. If you’re a strong seller, then you might look for opportunities to work on bigger accounts or those with more growth potential. If the account has multiple subsidiaries, then CSMs who have more experience with stakeholder management are a natural fit. These accounts have lots of cooks in the kitchen, lots of coordination between different departments. You’re moving away from customer education and enablement. So if you love people management, and keeping stakeholders (internal and external) aligned, this may be a good fit for you. 

Aisha: What are some early stage company red flags? What questions did you ask the CEO of the 6 person company?

Karla: To be honest, I didn’t know what to ask back then! 

One thing that’s not a red flag: an early stage startup that doesn’t have everything figured out. These present really great learning opportunities so long as you’re hungry and curious and willing to think outside the box. 

Though in retrospect the 6 person startup I worked at wasn’t hugely successful, it was a great stepping-stone for me. I got to wear a lot of hats that ultimately helped me form my own philosophy about the CSM role.

One red flag I wish I had known to look out for: lots of team attrition. Another is negative customer reviews for the product on blogs, Reddit. There may not be much written about them on G2Crowd or in Gartner Magic Quadrants,, but what those early-adopters are saying is a good signal about P-M fit. 

Overall, early-stage offers CSMs a lot of influence and a lot of opportunities to make a big impact.

Choosing the right company for your skillset and your growth is a daunting decision, and I hope you can apply some of this advice on your decision making. My goal was to provide you with practical, insightful tips on how to choose your next role. Good luck in choosing your future endeavors, friends!