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How to Hire the First Sales Leader for Your Startup

Kristin Bachman
8 min read

You've had a successful launch, your product or service is taking off, and now it's time to shift focus to acquiring new customers.

This accelerating momentum is usually a good indication that it's time to hire an effective sales leader to grow and scale your go-to-market strategy.

According to First Round Capital, "In 2015 and 2016, engineering leaders were far and away the hardest executive hires to make but. . . [now] sales leaders became the most coveted and difficult hires (with 26% saying sales was the hardest vs. 24% saying engineering). This looks like the start of a sea change as more enterprise companies enter the fray, compete for talent, and see firsthand how costly a bad VP of Sales hire can be."

Today, 74% of companies who admit they've selected the wrong person for a position lost an average of $14,900 for each wrong hire–not the amount of money a startup can afford to lose.

Defining the right sales leader profile is critical for your startup's growth and crucial to get right the first time around. This post will guide you toward doing it.

Key insights include: 

  • Why hire an early-stage sales leader
  • Mistakes founders make when hiring
  • 5 keys to hiring an early-stage sales leader
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Why hire an early-stage sales leader?

Selling is, of course, necessary for any business, but it is especially the case for startups. 

Founders organically adorn the sales cap, assuming the role to take an off-beat idea or vision, bring it to light, and sell it to investors, employees, friends, and families. 

After some time, when you have a viable product and seed capital, you need someone to find five to ten customers who are willing to take a chance on a brand they've never heard of or a product without a track record of success. 

This is one of the hardest tests a startup faces because there's a certain intensity, speed, and flexibility needed to sell startups successfully–and it's often underestimated.

Currently, Salesforce research shows that the average time for conversion from lead to opportunity is 84 days, with an average conversion rate of 13%. Out of that 13%, less than 1% of leads end up as real customers. 

For early-stage founders, the big question becomes: how can you find a fit with your first few customers before burning through your cash? 

What to look for in an early-stage sales leader

In the early stages, the right profile of a sales leader must be able to convince people to take a chance on something that might not be proven to work.  

There are a few essential characteristics to look for when hiring:

  • Charisma. Winston Churchill, Gandhi, Steve Jobs–some of history's most effective leaders share a dynamic, inspirational, and charismatic personality. They have extraordinary communication skills and command attention wherever they go.
  • Passion. Hiring people who aren't invested will end up costing your business an excessive amount of money and time. Having a sales leader who's passionate about client experience and satisfaction, establishing rapport and relationships, and believes in your mission is critical. 
  • Digitally-savvy strategists. Digital (and spending) is changing the world, fast. Hiring a sales leader who can keep up and can clearly demonstrate strategic thinking that is backed by data and technology will launch your business farther in the future.
  • Analytical. Startups live and die by numbers. Numbers are needed to analyze employee productivity and hiring forecast, to plan operational expenses, sales pipelines, and marketing investments. Every decision that a leader takes needs to be based on one or more of these numbers.
  • Persistent go-getter. Upsell, down-sell, cross-sell, you name it, they can sell it. Your sales leader will be selling in an alien landscape. Are they willing to do what it takes to find opportunities? They need to be able to penetrate any account and build long-lasting relationships with clients, all while representing a visionary product. This trait will also help them create immediate value.
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Common mistakes founders make when hiring their first sales leader

70% of SaaS's first VP Sales don't make it to 12 months. It's one of the most common and also the most devastating mis-hire in startups. 

There are six mistakes most founders make when hiring:

1. Hiring for pedigree over culture fit

The best of the best sales leader needed doesn’t only mean someone with an impressive resume, but most founders are too quick to assume it is. However, a sales leader who comes from a successful sales tenure at a Fortune 500 company in your industry might not be able to reach the same level of success in an environment that requires them to be nimble and experiment.

2. Failing to accurately assess candidates

Just because someone sold creative software doesn't mean they can sell all creative software. One product might focus on helping content creators create, whereas another might focus on assisting them in distributing it. Understand a candidate's core strengths, map them back to your business needs, and then assess them for fit.

3. Jumping to an offer too soon

As a founder of a young company, it's easy to get really excited over someone you've met. You want to bring in a sales leader with the expertise your business lacks, and you're under a good deal of pressure to get it done. Yet, offering up a chance to work by your side before a candidate has even had a chance to fully understand or comprehend your business or role is an easy way to create more stress. Plus, people lose interest in opportunities because they don't know enough.

4. Lingering on hiring decisions

Delaying and all the things that come with it–tapering off communications, starts, and stops in the hiring process–will help your candidates lose interest fast. 

5. Not seeing there are multiple ways to solve functional hiring problems

Don't expect your sales leader to be a magician. Consider your current team's strengths and weaknesses and identify the gaps to fill. More on this down below. 

6. Stop educating candidates

At every candidate touchpoint, you should be teaching them about the benefits of joining your company. How will your business help them further their professional development, even when they leave? What experiences will they gain? Always align the benefits to what they're passionate about. 

If you can avoid these common mistakes, you'll have a much better chance of finding the right leader for your stage of business.

5 keys to hiring an early-stage sales leader

1. Get a clear understanding of the role

You'd be surprised at how many founders don't take the time to truly understand what sales leader they need.

Three key questions to ask will help provide clarity on why you're hiring a sales leader: 

  • What does my business need at this stage? 
  • What are our projections and business goals in the next 6, 12, 24 months
  • Who are we selling to?

You can use two frameworks to help map this out further and determine the type of candidate needed: 

The leverage-based approach works best at the seed, and Series-A stage. You can use it to buy-back time (identify and chart your monthly lowest output work to determine the resources you need to find/outsource in your sales leader.) Or, you can use it to determine your company's highest priorities, map to existing strengths, and then overpay for great talent to balance the weaknesses. 

The second framework is the needs-based approach, which helps you identify gaps in your business (and then hire to fill them.) This approach is excellent at any stage and includes:

  • Reviewing similar companies in similar industries one step ahead.
  • Mapping organizational charts and defining gaps.
  • Charting your company to define strengths, weaknesses, and needs.
  • Meeting with leaders who have scaled these types of companies to further assess mistakes/pitfalls.
  • Defining and prioritizing business objectives/needs to hit the next fundraising cycle.

2. Build a robust pipeline

With a clear read on the role, it's time to turn to your network and open up talent pools to build your pipeline of candidates. 

Most people are willing to help, sometimes you just need to ask.

The "ask" is an incredibly powerful thing, and when you have someone in mind for a role and don't have a direct relationship, try leveraging your first-degree connections to make connections.

To start, leverage one of your most significant assets: your investors. They're well-connected, influential, and successful, and have been down the road you're on before. 

Help them understand what you really need because the more engaged your investors are, the more active they will be to help you out. 

Or, when you're raising your next round of capital, hand-select 4-5 angels who are in markets outside of your business. Get them involved in your next round and target people who don't work or live within a 50-mile radius of your business. 

You want to open network effects that you don't already have and with people who you don't know.

When approaching candidates:

This is one of the many excellent benefits of network effects. Have someone foster the introduction and be strategic when wanting to connect with candidates.

You'd be surprised at how often this step is missed but always include a reason for the introduction and show value for the prospect and to protect your contact's relationship with the person you want to get in touch with.

When you have that coffee meeting, or when you're waiting at the gate in the airport, be on the lookout for smart and capable people.

Building relationships is something you always have to be doing and not something you start when you need to make a hire. You never know when a coffee meeting can become an executive hire in one or two years.

This is the future of talent.

Hunt Club leverages the networks of over 10,000 experts and business leaders to help you hire the right sales leader for your stage of business. Get in touch to learn more.

3. Do put a sales leader candidate's passion over pedigree

Keep in mind that someone's passion and ability can throw pedigree or experience out of the water in your growth-stage environment. 

As a cash-strapped, growing business in the tech space, for example, it's hard to compete with Facebook to hire sales leaders for your team since you likely can't offer the same compensation or benefits packages.

Instead, place your business where it can stand out from the crowd. Think about networking with peers and colleagues, local college alums, and even family members of spouses in highly-dense startup areas who may want to move back at some point.

Hiring your first sales leader careful consideration. Just don't dismiss or overlook talent just because it's not where you'd expect to find it.

4. Get them interested, first 

Once you've found the people you want to speak with, how do you get them involved in what you're building?

The trick is that most people won't turn down something they thoroughly understand, and they're interested.

The challenge is you get so excited about the person potentially joining that you make an offer way before the person really understands your company's growth plan, traction in the market, the role, hiring goals, product road map, and future financing plans.

It's the founder's nature to move and build quickly, but don't be too quick to offer a job to someone you've only just met.

Most people will be intrigued, attracted to, and curious about something only once they have the most information possible. If you find someone you would like to recruit for a job with your company, think about asking them for a coffee, then lunch or something outside of where you work, first. 

Establish a rapport with them and use the time to educate them about how you are building something that one day will change an entire category. Share the details about who you work with, your business projections, financial models, and plans to raise capital.

This fosters trust and real relationships with every candidate and keeps your business on their radar. 

5. Never stop educating candidates on your business

Think of all the ways you can inform candidates so much that in the chance they join your business, it's a seamless transition.

Find out as much as you can about the candidates you're speaking with. Most importantly, ask your potential candidates a ton of questions so you can get a good read on what the person is interested in, what they like doing, where they want to go in their professional journey.

Then take what excites them and align those things with what you're building and always show how your business can offer them a path to growth and their professional development.

Hire with precision and do it faster with Hunt Club

Hunt Club can help you find and hire strong sales leaders for the right stage of your business. 

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