Evolving from Founder-Led Sales: Modern Sales and GTM Reimagined with CloserIQ

Here at Notable Capital , we often get questions from founders about how to effectively scale their startups’ go-to-market strategies. When I first met Jordan Wan through Keegan Forte (one of the founding members of Chief NYC back in 2019), I was struck by how he now fields many of these same questions as a former operator-turned-investor.?

After graduating from MIT with dual degrees in computer science, Jordan started his career in financial services as a hedge fund analyst at Bridgewater Associates. In his next role as a GTM strategy and sales leader at Zocdoc, he recalls cold-calling when trying to sell into doctor’s offices. Even back in 2012, Jordan knew there must be a better way to build a modern sales organization.

Now as the founder and CEO of CloserIQ and an early-stage investor at CoFound Partners , Jordan is passionate about helping startups scale their go-to-market function. Though there is no one-size-fits-all template, I wanted to get some of Jordan’s insights on reimagining modern sales orgs and go-to-market strategies at startups:

Here are some highlights from our LinkedIn Live convo:

What are some common mistakes that early-stage founders make when evolving from founder-led sales?

For founders ready to hire that first salesperson or account executive, there’s a tendency to pass the baton prematurely—or as Jordan says, there’s the tendency to hang on too long and micromanage.?

Here are some strategies for a smoother transition:

• Start with full cycle hires: As startups scale, generalists can shift to becoming specialists. But based on Jordan’s experience, specialization can be premature for early-stage startups.
• Segment your target universe: In this case, Jordan says founders can typically shift to larger and more strategic accounts. To ease this transition, he recommends creating some internal standard operating procedures around how to determine when the sales rep should bring the founder into a deal (versus when that rep can pursue and close it on his or her own).?
• Stay involved: Consider waiting until your sales strategy is repeatable (more on this below!) before removing yourself from the process. Once you’ve established product-market fit, it’s usually easier for founders to back off a bit.

Source: CloserIQ

View CloserIQ’s full deck for more insights

What are some do’s—and don’ts—for building a modern sales org??

Here are three ways to successfully build a modern sales org:

• Assess your infrastructure and capability before you grow the sales team: As Jordan points out, it’s going to be that much harder “if you have no methodology, no CRM, and no kind of ideation yet on how you're going to teach somebody else to take over for you.” Spending a little bit of time to “put some general guardrails around that is going to be helpful.”
• For seed-stage startups, it’s all about testing: “Try to double down on the channel that works, rather than try to make everything work,” Jordan says. This way, when you get to your Series A or Series B, you can do so with one core go-to-market motion.
• Think about what can really help drive repeatability and sturdy economics: Questions like “What is your average contract value?” will help you determine which go-to-market options are available to you, Jordan says.

What are some best practices for structuring a sales org chart?

Most startups have a bottom-up sales situation, starting with one salesperson and growing from there. Jordan’s take: “Until you start to see revenue creation being a repeatable science as opposed to an art, you probably want to go a bit more bottom up. That's a better way to build the org and be a bit more intentional.”

How can founders tell when it’s time to build out a modern sales org? Ask yourself:?

• How much time are you spending on sales calls and sales conversations? If it’s about 10 hours a week or more, chances are “you’re starting to shift toward being able to support someone doing this on a full-time basis,” Jordan says.?
• What is your actual bandwidth? If you feel like you’re dropping the ball on opportunities or not tracking them properly, you may be ready to hire.

As always, assess what your needs are—and what your customers are telling you. Determine where you want to spend more time. And then hire accordingly. “Be very, very specific when you go out to hire,” Jordan says. Successful hiring doesn’t have theoretical objectives.?

When might a fractional sales leader make sense for your startup?

For seed-stage startups, a fractional sales leader may be ideal “because at that stage, what you need is really 95% execution and 5% strategy,” Jordan says. You might not need or be ready for that expensive full-time hire.?

You can also consider pairing a fractional sales leader with an existing sales team, even if it’s just one other person. As Jordan points out, “there are a lot of great fractional sales leaders who often are happily full-time employees who will allocate a couple of hours a month, or even a couple of hours a week, to do startup advisory and guidance.”?

This can be “the best of both worlds” because you get strategy from a fantastic sales leader in your industry (or an adjacent one) and “still get your dollars pointed toward the execution, which is what is needed.”?

How do you create a repeatable sales process anyway?

It’s a great question, but a bit of a trick question, Jordan says. Like product-market fit, building a sales process is “an ongoing continuous journey of perfection. So you may have built a repeatable sales process for Product One at the very beginning. And then when you expand into Product Two, you start finding that you don't have product-market fit, you don't have a repeatable sales process, and it starts all over again.” You’re not quite reinventing the wheel, but you might not have the same success immediately if the product is slightly different.

To mitigate any potential pitfalls, Jordan suggests that founders lean into the idea that sales is the No. 1 priority. At the end of the day, “someone has to watch the money that comes in and the money that goes out,” Jordan says. “You can never really outsource it or delegate it to a sales leader.”

CloserIQ is an executive search and recruiting firm that has scaled 900-plus startups, including Justworks, Oscar Insurance, and Riskified. Subscribe to CloserIQ's monthly newsletter to receive the latest industry insights and best practices on building a world-class GTM organization.

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+ Special thanks to my colleagues?Amy Chen ?and? Sabrina D'Alessandro who made this come to life!