The VP of Sales (When, Who, and How to Hire)

Ally Gsell
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The Ultimate Guide for Founders and CEOs

Many tech companies are destined to fail from the early days. You may have a great vision and a unique product or service, but if your background is primarily tech- or product-development-focused, you are likely to make mistakes (sometimes fatal) in hiring and training.

Even if you have tight goals and an excellent system for capacity planning, the human aspects of sales hiring can ultimately trip you up.

SaaStr says that 48 different types of sales leaders exist. That may well be true. People are as varied as snowflakes (and often as susceptible to melting under heat).

But we’ll break it down to some basics, so you will know precisely when and how to hire talent and, most importantly, pinpoint the WHO to help you achieve your (often ambitious) growth goals.

When to Hire a VP of Sales

In short, you should hire someone as soon as you can afford it. Founders are usually not sales experts, so whoever comes in will probably inherit a flawed process -- systems, messaging, and expectations. Deals and prospects may not be properly tracked (if they are tracked at all).

Businesses have very different needs, depending on their product/service, revenue targets, culture, and Board/investor expectations.

The Early Days

When you’re first launching, you can probably get by with a small, talented, and high-performance team that understands your offering and has related experience in your category and target market.

You may be cash-strapped at this point, but don’t hire on the cheap. You’re also building your brand image, and buyers can tell when a rookie is cutting their teeth.

Decision-makers are pressed for time. If your product is complex and expensive, your target market wants to know that they are dealing with pros. No one wants to be a guinea pig or lab rat for a brand new SDR/BDR.

And remember, everyone on your team is ultimately a salesperson. Encourage your team (no matter how small) to stay active on LinkedIn, lookout for new prospects, and present your company in the best possible light.

Scaling Up

Perhaps you’ve gotten some funding, or you’re absoluting crushing your sales and growth goals. You have a few reps. They love what they do, you love what they do, and you see the company thrive.

You don’t have the time and expertise to manage the team, so you need to create a layer between you and them. Re-organizing is a CRITICAL decision.

Promoting from within may create tension, but you recognize a person who has talent, which is good for others to see. But, be wary -- just because someone is a great salesperson doesn’t mean they are a great leader.

Many sales directors pick up bad habits from bad managers they have worked for in the past. This role is a combination of cheerleader, motivator, trainer, and results reporter/aggregator.

If you’re bringing someone in from outside the organization, get feedback from team members during the process. No one who’s been working independently wants a “boss,” but if your salespeople are involved in the decision-making, and you’re transparent about your process, they’ll be more likely to get on board.

Remember, you’re still growing at this stage, so be sure that person is willing to get their hands dirty and serve as a role model and trainer for the rest of the group.

Reaching the Big Leagues

Whoa! You’re finally a grown-up company. You’re ready for a VP of Sales. This may be the most challenging job in your company, so choose wisely. This person will be responsible for:

  • Helping to set sales goals and timing.
  • Capacity planning (which is often overlooked but is business-critical).
  • Working closely with your Marketing lead on building sales funnels.
  • Reporting results to your Board and/or investors and building action plans when they are missed. (Everyone has been there.)
  • Hiring, training, motivating, rewarding, and (sadly, sometimes parting ways with) sales professionals.

In short, it’s a critical mixed bag of financial, sales, and people skills.

You should look for that person at least six months before you think you need them. Work with an HR specialist (either in-house or outsourced) to craft that job description and set of skills and interview carefully and objectively for a person who will be an ideal “fit” with your product, culture, and needs.

Make sure your Marketing lead is involved in the process! If Sales and Marketing are not on the same page from day one, tension, finger-pointing, and financial disaster may ensue. You don’t want a broken funnel!

Who to Hire as Your VP of Sales

If Saastr is right and there really are 48 different types of VP Sales, you have to make sure your best candidates are the right type for your business. Here’s the golden rule for getting started -- hire someone for the right stage with the right experience.

Sasstr describes 4 ideal candidates:

  1. The Evangelist: Someone who is passionate about selling, but may never have actually closed deals themselves
  2. Mr. Make-It-Repeatable: The unicorn of sales leaders; adept at replicating and scaling
  3. Ms. Go Big: Not quite as hard to find as Make-It-Repeatable, but able to get a company from smaller deals to enterprise-level selling and grow a team
  4. Mr. Dashboards: “Looks good in a suit” but may not really understand the nuances of sales process and leadership

Next, this candidate can have one of two competitive experiences, 3 different backgrounds of deal experience, 3 different types of experiences in deal sizes, and 2 different types of leads or customers! This is how SaaStr gets 48.

An AE may have had an exceptional sales record but no experience managing people. If you are invested in a candidate whose skill set has gaps, commit to training and coaching to help them “grow up.”

Some common misconceptions:

  1. Someone who is great at selling will make a great Sales VP. If someone doesn’t have soft skills, analytic capabilities, and relationship cultivation chops, they are destined to crash and burn.
  2. Someone who is a great leader will make a great Sales VP. Some time spent among the sales weeds, hiring/motivating salespeople (and a willingness to get dirty hands) are critical to this role. Great sales leaders can move nimbly between strategic, tactical, and relationship roles.

Be open-minded in your hiring. For example, a seasoned and mature leader can be trained on your product. Create a balance between women and men. Don’t immediately shut out a candidate because they don’t fit your mental image of that VP role. Remember, you’re hiring someone whose skills may complement yours, not a brother/sister/buddy.

And remember, salespeople excel at selling (duh!), so you need to be sure candidates are not all sizzle and no steak. Ask tough financial questions, probe on times when they may have missed quota (and what they did about it), how they manage challenging situations with their teams, and other “human” questions.

VPs are leaders and not “one of the gang,” so watch for language that may indicate that someone is more about “me than we.” Team culture is critical to success.

Effective Onboarding

This process starts even BEFORE the offer is extended. You want to ensure that the expectations of the role are adequately managed. When you’ve narrowed down your choices to one or two candidates, share your sales goals with them and ask them how they would tackle the challenge.

Make sure you’ve invested in the right tools for reporting and forecasting. If your new VP spends more time with Excel spreadsheets than with prospects and team members, you’ve got a problem.

Just because someone has a VP title doesn’t mean that they are above doing some heavy lifting. Your VP should be directly interacting with top prospects and learning as much as they can about the sales process.

If you’ve been handling sales yourself, you must also be willing and able to step aside and let your new hire do their thing. No one wants to be micromanaged, but you need to remain involved enough to know what’s going on. Above all, do NOT create a rift between your Sales VP and their team by doing constant end-runs and asking team members about how their new leader is doing.

Onboarding doesn’t stop once someone is settled into your company. Over time, your business needs may change and whoever you hired needs to step up, expand their skills, or move aside. Be honest with yourself about whether that VP has the desire and motivation to help take the company to the next level of growth. If not, make some tough decisions.

Remember too that any professional, at any level, thrives on positive reinforcement. When your VP hits or exceeds goals, celebrate! True sales leaders are always in demand, so you want to be sure that you think about retention 24/7/365 and deliver rewards that meet each individual’s needs and goals.

Breaking Up is Hard to Do

We’ve all been there. You’re in a rush to fill a role, and you realize 30, 60, or 90 days in that the person is a “mis-fit.” Or, you just got a significant funding round, and the person who was terrific with your previous forecasts or target markets may not be able to bring the team along for that new BHAG (big, hairy, audacious goal).

Be honest, move quickly, and communicate effectively and professionally to the rest of the organization why you’ve made changes. Most importantly, have your contingency plan in place before you deliver the news.

In Summary…

Knowing when to hire that sales leader is as important as who you hire. Give them the support they need to contribute to the organization. Communicate and reward.

And invest in the right tools to forecast and hire. You want that tremendous new VP to spend their time helping grow your business, motivating their team, and not sweating over spreadsheets.

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