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Dan SchoenbaumOperating Advisor

How to Hire Your Startup’s First Sales Lead

A great product is the foundation of a great business. And yet, throughout my decades-long career, I've witnessed a repeat pattern of brilliant technical founders who put all of their energy into building a fantastic product and never achieve success.

Why? A strong product needs to be paired with a strong go-to-market strategy.

It’s true that your product is the foundation of your success, but sales and marketing are critical for driving scale. Both departments play key roles in turning your product into a powerful growth engine—defining your target customer, crafting a clear message focused on impact (not capabilities), and helping clients realize value as soon as possible.

If your skillset as a SaaS entrepreneur leans toward product, like most founders, you need to balance your expertise with smart sales and marketing hires. Paired with a strong product-market fit, the right talent will enable your company to hit the gas on growth. As a follow-up to my previous article on hiring your first marketer, this piece details the key things to know when it comes to hiring your first sales lead.

Focus on product-market fit before hiring

Here’s an uncomfortable truth: A salesperson is not a silver bullet solution to making more sales. If you don’t have product-market fit, a sales hire is going to struggle to find the right target and convert customers.

According to Forrester, three out of four B2B buyers want to self-educate to learn about products, rather than talk to sales reps—so think of your product as your very first salesperson. A product-led growth strategy entails showing customers the value of your offering, rather than telling them: Let the product speak for itself through a freemium version or a timeboxed free trial. Then, once you have a compelling product experience to offer potential clients, hit the gas on hiring.

Don’t wait too long to take advantage of your market opportunity: Almost every founder I’ve met under-invests in their go-to-market strategy and misses out on valuable momentum once they reach product-market fit.

Don’t underhire or overhire

Early-stage companies have limited resources, and founders often try to save money on their initial hires by bringing on a junior person. But it’s hard to sell a startup product—especially in the early stages. You need someone who can figure out the right message, the right approach, and the right tactics on their own.

Alternatively, some startups swing for top talent, but end up bringing on someone who’s a leader, not a doer. Hiring someone too senior may offer expertise, but without boots-on-the-ground energy, you likely won’t benefit from their knowledge and experience as fast as you need to.

Be cautious of under-hiring or overhiring: You need someone who will help shape strategy, as well as pick up the phone and pitch potential clients. They should be willing to roll up their sleeves, work through long prospect lists, learn from the conversations, communicate their insights, and figure out how to build a sales model. You can also work with an investor, like our team at Elsewhere, to bring on an experienced Operating Advisor who can advise more junior or mid-career hires.

What to look for in your first hire

There are two critical qualities in an initial sales hire.

1. Familiarity with early-stage challenges

One of the most important qualities in an early hire is someone who has successfully navigated the waters you're about to enter. (This is a great way to approach bringing on board members, as well.) You want someone who knows how to walk the challenging path of building an early-stage sales pipeline—from leading with the product, to building the message, hiring a junior team, and creating a healthy culture.

If you look for someone who has experience building out a multi-billion dollar sales team, they're likely not going to be a good fit because that's a completely different challenge, even if they have experience in your market. While domain expertise is important in a software space, it's more important to hire somebody who has been at your stage and successfully navigated through that.

2. Ability to create a strong company culture

A large part of a sales leader’s role is relationship-building. You want to look for someone who can create an enduring culture—not only with employees, but also with customers.

If you have someone who leads through intimidation or instilling fear, it will become hard to hire and retain a good team (and, trust me, the rest of your company will be impacted by the negativity created within the sales team). ).

Culture ultimately comes down to communication. Eventually, the hire should be able to synthesize challenges from the field, share them with the executive team, and work through them with the entire team. You want someone who inspires others to think differently and establishes a strong sense of trust in their collaborators.

These two qualities may sound obvious—the right experience and leadership qualities—but I see so many failures in sales reps and sales leaders, because founders get distracted by someone’s multi-billion dollar track record or their history at the hottest company in the space. Don’t get distracted by shiny resumes (for example, a stint at a hot company); focus on what you really need within your own company.

Trust in the importance of good talent

If you make a mistake in sales (or marketing) hires, it can set you back six months to a year in terms of your progress—and you can blow through a lot of capital in the process.

On the other hand, making the right hire at the right time will transform your business in the other direction: catapulting your growth and company trajectory in ways you might never have imagined. Invest your time, energy, and resources into finding the best fit possible for your early-stage B2B startup, it’s well worth the effort.

Interested in more guidance on hiring for go-to-market? Check out our other post in this series on hiring your first marketer.

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About the Author

Dan Schoenbaum

Dan is a repeat CEO & COO of high-growth companies, the founder and Managing Partner of High Tide Advisors, an Operating Advisor with Elsewhere Partners, and a product-led growth advisor.