How Early Stage Startups Can Get Set Up for Customer Success

Cassie Young
Operating Partner
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Interview Highlights:

  • Customer Success is something VCs want to see founders move fast on
  • When pitching, place your best customers up front and make them available for investors to contact
  • Make talking to customers a part of your daily routine, no matter what stage your company is in

Across her career in investment banking, growth marketing, SaaS leadership, and most recently leading Primary Venture Partners’ Portfolio Impact Program, Cassie Young has seen customer success—and failure—from just about every possible angle. 

In this interview, she shares a few of the most essential tools for setting your customer success strategy in the best direction. Some of those tools are straightforward matters of documentation: ideal customer profiles, customer value plans, and the “NASCAR” slide showing prospective clients all your satisfied existing accounts. And then there’s this simple—but too-often-forgotten—advice: Talk to a customer every day. Don’t take any shortcuts when it comes to getting to know them and their needs.

Can you tell me a bit about yourself and Primary Venture Partners?


Primary Venture Partners is an early-stage venture capital fund focused exclusively on companies in New York City. We invest in companies raising their seed round, then we reinvest in them as they grow and scale. We’re about six years old as a company, and we’re industry agnostic. We have about 50 active portfolio companies today that run the gamut from enterprise SaaS all the way through to e-commerce. 

Our model is a little bit unique, and I’m sharing this because it will help explain how I landed there. We’ve borrowed a little bit from the growth equity and private equity world by hiring full-time operating partners to work at the firm to help our portfolio company. 

I am one of the operating partners at the firm. 

I spent 15 years as an operator on the client side before making a leap to the VC side one year ago. Most recently, I spent close to 7 years at an enterprise marketing technology company called Sailthru. I was the Chief Commercial Officer there, which functionally was the CRO, but CCO sounds a little less salesy (laughs). I led our global customer success teams as well as our global sales organization. 

The operating partner role is just that—it’s finding people who were C-suite level executives to come in and work with our companies when they’re in the earliest stages, before they have the resources to make those hires themselves. It’s a unique role in that I spend 80% of my time in the field with our portfolio companies. I help them with anything that touches sales, marketing, and customer success, and the other 20% of the time is spent on traditional venture capital activities.

What are the boundaries in your role as an Operating Partner? How much influence do you have over the companies you work with?

That’s a great question. We call our program at Primary the Portfolio Impact Program. The way I describe this is that we’re basically a customer success team. I use SaaS analogies for most everything my team does at Primary, regardless of whether it’s go-to-market or finance. Our job is to do what a CS organization would do, which is to be a proactive extension of the portfolio companies’ teams and understand the unique objectives of their businesses. 

Quite frequently, a portfolio company’s objective is to raise a successful Series A, so we will understand the nuances of their business and help them develop a “value plan” to get there—maybe that is building a predictable/repeatable pipeline engine, etc. 

Sometimes private equity gets a bad rap for being something of an invisible hand that dictates a playbook that founders must follow, but that is not what we do, and we’re very clear about this with the founders we work with. We tell them our job is not to be prescriptive, but to try to spare them some of the headaches that we’ve seen founders hit before, and to prevent them from reinventing the wheel. We work for their benefit, but we work for them.

So what role does CS play when you’re evaluating potential investments?

CS is a massive consideration. Because we’re an early stage shop, we’re super focused on what we call the seed to Series A graduation rate. 

In my opinion, there are three areas that software companies need to think about on the journey to Series A. 

  • First, they have to prove that they’re not relying on the founders for everything. So not just relying on founder-based selling. They can hire and scale. 
  • Second, they have predictability and repeatability in the go-to-market engine. This means they can build the pipeline and close deals in a predictable way. 
  • Third pertains to the product and the customer. CSAT and/or NPS have to be strong, which is important for a few reasons: Retention is the cheapest form of growth and having happy customers fuels the whole business, and high CSAT suggests that something about the product and service is going well.

I regularly say that businesses must do everything in their power to make their customers successful with their product. If you do that, you’d have to catastrophically screw something up to not succeed as a business. 

What do you do in situations where their CS needs a lot of improvement?

Because we’re such early-stage investors, it would be unusual for a business to have really poor CS to the extent that the issue is unrecoverable. These businesses usually just have an early set of customers. Maybe they’re not the right customers or maybe they can’t convert them, but we are early enough into the journey that we can figure things out. 

Also, I subscribe to this school of thought that everything is solvable as long as you’re committed to fixing the problem. I frequently say, “sunlight is the best disinfectant.” Bad news is actually good news: You just have to understand what isn’t working correctly in order to devise a plan for how to fix it. 

When I first started my role at Sailthru in 2014, our Net Promoter Score was negative 26. We had a moment where we thought, “People hate us more than their cable company!” But we unpacked that and sliced and diced the data. We read all the qualitative comments and went on a multi-year journey to address the feedback. A few years later, we had improved NPS by over 60 points. So it was fixable. 

I actually love working with earlier stage companies because it’s easier to right the ship in that stage. 

When something looks off with the customer base, we coach people on how to investigate the gaps, and how we would reorient the whole company around making it work. It’s not just one person’s job; the whole company has to help get it right.

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What are the most common CS mistakes you’ve seen?

When an early-stage startup encounters a customer who will pay for their product, they’ll usually take them on regardless of who the customer is (or isn’t), purely because a check is a check. 

As software companies mature, it is imperative to understand the ideal customer profile (“ICP”) and to double-down on that market segment. All too often companies wait far too long to really identify and lean into a beachhead.  

Another common pitfall for early-stage companies is to get caught up in Challenger Sale methodology far too early on. Yes, at some point businesses will need to teach the customer why they must buy; but in the early days, startups should focus on finding the people who are willing to be early adopters and who do not need hours of convincing around why innovation is relevant. Sometimes startups work so hard to fit square pegs in round holes to close deals that they wind up distracting themselves from higher-leverage growth activities. In the early days, you have to find the subset of the market that wants to have a behavior change and wants to buy into the product. Then you can learn from that and evolve to challenger-selling from there. 

I recently worked with a company that was committed to selling $100K contracts. Their growth stalled, and they then retreated to signing $20K contracts because they found decent sales velocity with those contracts. I told them I’d be skeptical of the decision to change course until they could show me the downstream evidence that those customers were as sticky and successful as the larger customers we had previously targeted.

When assessing performance by customer segment (contract size, industry, etc.) it is important to understand the nuances of how they perform as customers: Are they totally unprofitable from a time consumption perspective? Are they happier from an NPS perspective?

When I was in the marketing world, I frequently preached the importance of marrying retention data with acquisition data. I tell software companies the same thing: You have to marry customer success data with your sales and marketing engine to make sure that you’re really doubling down on the customers who are going to be the right long-term partners for you. Detractors are five times louder in the market than promoters. They’re just not worth it just to get a customer in the door. 

What if you’re a founder that’s still pitching? What’s the best way of communicating to VCs that you’re doing CS right?

The best thing you can do is to highlight who your earliest customers are and share some signals regarding early customer satisfaction or NPS; ideally you should also offer investors the opportunity to talk to customers directly. 

I’m going to share one of my favorite “mic drop” moves from when I was selling software. At the end of the pitch meeting, I would throw up a slide that had 20 photos of customers with their names, titles, and email addresses. I would say to the prospect, “No one tells our story better than our customers, so no need to take our word for it. Call any one of these people and I’m sure they’ll be happy to speak with you.”

Guess what? My understanding is that no prospect ever called anyone from that list. So I often tell portfolio companies and founders I work with to throw the customers up on the screen. The “NASCAR” slide is critical.

Are there any final words of wisdom you can impart to our readers?

There are a couple of things I would offer as advice for startups: 

First, you have to invest the time to get out in the field with prospects and customers. 

When I was an operator, I had a rule that I had to meet with at least one customer every single day of the year. Usually that was more like two or three customers per day, but my commitment set the tempo for the whole organization. If I can make time for this, you have to make time for this. You have to be out in the field with the customer. 

As founders build their management teams, we still want them (the founders) to be out in the field and meeting with customers, not just relying on their leadership team to do so. Similarly, meeting with customers is not just a sales or customer success job; your product and engineering teams also need to get in front of customers, even if that means bringing customers into your office for a working feedback session. And remember, in the early stages it’s almost always okay to do stuff that’s not going to scale. You can untangle yourselves from that later on, but going “all in” for customers is critical for cultivating a pool of early promoters. 

Finally and most importantly, I’ll caution that all too often customer success becomes about relationship management, and that is very, very wrong. Companies must be focused on customer value drivers from the very, very earliest stage—not purely relationships. When I get on a call with a CSM that’s talking about the weather and asking if I have any questions about the product, I have a negative reaction. I want them to talk to me about my unique objectives as a customer, and what two or three things my team can focus on to move the needle in the next 60 days. All too often CSMs approach the engagement from the angle of, “Here are dozens of things the product can do for you,” and nothing gets done in the process. I call this the “boiling the ocean” effect. Instead, the CSM should use a customer value plan (ideally an artifact that is started during pre-sales) to focus the customer on two or three tactics at a time. Once those are complete, you can pick two or three more from that list of a few dozen. Keeping the customer focused and reinforcing your understanding of their business objectives are critical ingredients to effective customer success.

Primary Venture Partners

Primary Venture Partners is a seed-stage venture capital fund based in NYC. The fund is run by Brad Svrluga and Ben Sun, who have a combined 30-year track record as successful investors and operators. Primary offers unparalleled experience, resources, and networks for New York’s most promising founders. The fund serves as the first call for its portfolio companies, dedicating significant resources to best position its companies for the journey from Seed to Series A and beyond. From the Primary Expert Network, a network of over 200 seasoned technology operators and functional experts, to a Talent Program headed by NYC Tech recruiting veterans, Primary helps its founders solve their biggest tactical problems and build world-class teams from the ground up. To date, the Primary team’s successes include seed investments in, Ticketfly, TxVia, Mirror, and Coupang, and it counts some of New York’s most promising startups—including Slice, K Health, Chief, Ollie, Latch, and Vestwell—among its portfolio.

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