Hiring the right Head of Sales is a difficult decision for most early-stage companies. Knowing what to look for can be tough. You want to make sure the leader has a high-likelihood of success with your company. Learn more about how to hire the right head of sales for your team.

When you are looking for a Head of Sales, be careful about which type of sales leader you are hiring. Not all sales leaders are created equal.

I like to use the analogy of a Track & Field team. You are the Track coach and you need a runner. You can’t just pick any runner for the race. Runners are specialized. The 100-meter runner. The 800-meter runner. The marathoner. They are all runners but they have different skills.

You can’t put a marathoner in a 100-meter race and expect them to win. They will get torched. Same goes for the sprinter in a marathon, they will tire out before the 12th mile. It is rare to find a runner that can compete in all races. That person may not even exist.

The same is true for sales leadership. When you are hiring, you want to make sure you have the right “runner” for your race. Sales leaders with experience selling software to small businesses are going to have a hard time building your enterprise sales motion. Leaders that have only run sales teams before are going to struggle if you give them a customer success team in addition to sales.

This isn’t to say that leaders’ skills are static. People learn new skills and adapt to their environment. It’s best for sales leaders to have responsibility beyond their zone of competence. If you are going to saddle your sales leader with more responsibility, you better make sure that your core sales need is an exact match for their core competency.

For example, if your core business grows through enterprise sales but you want to move down-market, hire the enterprise sales leader. Steady the ship and make sure the core business is growing. This gives you permission to expand into a new part of the market with a new selling motion.
‍

How to evaluate executive sales leaders

When choosing a Head of Sales for your company, be disciplined on the front end about what you want and what you don’t want. Use a common set of objective characteristics to evaluate each candidate.

Start by looking at your own business and defining the absolute perfect candidate. This candidate will be a 10/10 on fit for customer profile, demand type, sales cycle, deal size, rep profile, etc. It’s unlikely that you will get a 10/10 candidate, but at least you know what to look for in your evaluation process.

Here are some tactical categories for evaluating your current business and sales motion:

1. Customer profile and source of demand
‍
Who are your current customers and how did they buy your product? Your customers may be accustomed to using search engines to evaluate products and solve problems. They may prefer to go to conferences and meet with vendors. Your customer may be able to make quick purchasing decisions, or they may need to get buy-in across the organization to buy your product.

‍

Whatever the case, you want to target a sales leader who has experience finding customers in the same way that you found most of your core customers. A leader who loves going to conferences to drive business is going to have a difficult time building an SDR motion to drive demand. The customers’ buying process are so different that its difficult to translate those sales leadership skills from one to the other.

Some questions to ask:
- Who buys the product: role of exec buyer, role of champion, role of evaluator, etc?
- Where does demand come from: inbound, outbound, field sales, referrals, etc?
- How does the buyer make decisions: individual, by committee, how many people involved in the decision, is a trail or proof-of-concept required, is a sales-engineer required, etc?
- How is the product implemented: is this a land-and-expand style adoption, is implementation technical or does the customer self-onboard, etc?
- How is the customer supported after implementation: is customer success needed, what does customer support look like, how do you run regular performance and usage reviews with customers, is sales involved in renewal and upsell, etc?

2. Deal size and sales cycle
‍
How big are the deals (in average sales price) and how long do they generally take to close? Sales leaders have muscle memory when it comes to sales cycle and deal size. When you are used to selling to publicly traded companies, you can ask for large contracts and you are skilled at navigating a complex buying process. This does not translate to an SMB sales motion where the deals are $10k and the sales cycle is 14 days. Find the leader that has experience selling to customers of the same size and sales cycle of your core customer.

Some questions to ask:
- What is the average sales price of your 10 most recent customers?
- How long did it take (on average) to close your last 10 customers?
- Are deals monthly or annual? How long are the agreements?
- Does the customer sign a contract? What does the legal review process look like?
- Who is involved in the sale? Is there an SDR handoff process? Are there sales engineers?

‍

3. Team structure and sales rep profile

How you scale your sales team will depend on the team structure and the type of sales rep required to sell your product. Larger deals and longer sales cycles require a more sophisticated (read: expensive) sales rep. Smaller deals and shorter sales cycles require a less experienced sales rep.

Sales leaders who have had success scaling a team become proficient working with a certain type of rep. They know how to hire, onboard, and coach those reps to success. They know how to promote managers from within the ranks. Their elusive “playbook” usually works with a certain level of rep experience and sales acumen. It’s uncommon, for example, to find enterprise sales leaders who can coach up a team of SMB sellers. It’s almost like they speak different languages.

This goes hand-in-hand with the team structure. When you have a small group of skilled enterprise sellers who operate in the field, you want a sales leader that knows how to run that kind of team. Similarly, a gang of mid-market sellers in an office working together with an SDR team will require a sales leader that knows how to build a sales floor and a culture that leads to success in that sales environment.

The sales leader you hire should have experience working with the structure of the sales team you are looking to build and with the types of sales reps that are selling into your core customer base.

Some questions to ask:
- What kind of experience does our ideal sales rep need to be successful on our team
- How will our reps need to be onboarded to sell our product?
- How many reps are on the team?
- Is this an inside sales team or is it a field sales team?
- Do the reps focus on new logo sales exclusively? Or are they responsible for retention and upsell?

Pulling it together for the right candidate

Once you have outlined your core business and built your evaluation criteria for a sales leader, create a scorecard in an excel spreadsheet and rate your candidates across fit in each category:

- Customer profile
- Source of demand
- Deal size
- Sales cycle length
- Team structure
- Sales rep profile

You may find other criteria that are important for your evaluation, add those to the list. It’s all about what your business needs.

Some other things to consider when hiring a sales leader…

They get granular in the business

The best sales leaders can operate both tactically and strategically. On top of the executive responsibilities, they sweat the details. They pour over pipeline reports to make sure all deals are moving toward a close (won or lost). They are hyper-focused in the hiring process to make sure the right candidates are coming on board. They are jumping on phone calls with customers to drive more revenue, or to retain existing revenue, or to get product feedback. They meet with marketing to make sure the messaging is on point and that the demand is flowing through the door. They meet 1:1 with front-line reps to understand what is happening on the sales floor. They are present and available with the team.

Be wary of the dashboard jockeys that just want to look at reports all day. It’s easy to be stuck in executive meetings or strategy meetings or whatever the excuse is. But the best leaders know the way to drive revenue is to get on the sales floor and work with the team.

They know how to build a team, quickly

Successful sales leaders usually have a stable of 2-3 good reps that will follow them to the new company after they are onboard for 90 - 180 days. It’s OK to ask about this in the interview process. Learn about those reps. Why would they work with the leader again? What are the profiles of these reps and do they fit the model of your ideal sales rep?

Leaders are only as good as the team that they build around them, and the right leadership candidate for your business is one that can quickly get to work putting the team in place.

____

All of this is only scratching the surface. If it feels daunting, that’s because it is daunting. Hiring for leadership is difficult. The sales leader sets the revenue pace for the organization and has a huge impact on the company culture. It’s best to be measured and deliberate when you are looking for the right hire.

‍