Taylor ThompsonFinding the right leader to scale your sales engine is one of the most important decisions a startup executive makes. If you find the wrong person, it can be a “game over mistake” – you’re out $500K in salary and search, you bring on the wrong sales reps, and start moving in the wrong direction.
At Almanac we’re building a collaborative editor that helps teams keep organized so they can focus on the work itself. We partnered with CloserIQ to publish their workflow on how to hire a head of sales.
We recently sat down with their founder Jordan Wan to share his step-by-step process for hiring the right sales talent in person.
6 Steps to Hiring the Right Head of Sales
Here’s Jordan’s basic process, including links to templates you can copy and use in your own team:
- Step 1: Assess your sales context and what you think you need. Start by assessing where your team lies on the sales learning curve. Are you transitioning form founder led sales to a few AEs selling, or do you need a new Sales VP with experience going from $5 to $20 million ARR? Then, have leaders fill out the CloserIQ Head of Sales Responsibility Scorecard to make sure they’re aligned on focus areas for the hire.
- Step 2: Decide if you actually need a head of sales. As we’ve written before, startups often hire a VP of sales much too early. Consider three things: your initial self-assessment, your place in the sales learning curve, and your sales team’s size and complexity. Based on this, you can spot if you actually need a head of sales and, if so what level of manager you need (see CloserIQ’s sales manager leveling chart to help with this).
- Step 3: Run a gap analysis of your sales machine. Next, either have the founder or a sales advisor or consultant run through a detailed gap analysis of your sales team. Look at key pieces of the sales process to understand every aspect of your sales machine: strategy, funnel performance, talent, culture, motivation, and operations. You can follow Jordan’s checklist here for complete detail.
- Step 4: Develop a detailed hiring rubric based on this gap analysis. Then, translate the gaps in your sales machine into focus areas for your search, skills to look for and interview questions to ask (here’s an example of what this looks like).
- Step 5: Pick the right executive recruiter. Make sure to find an experienced executive recruiter – one who specializes in sales executives and has an existing talent pipeline. Here, Jordan shares tactical questions to ask, and red flags to watch out for to make sure you hire the right firm.
- Step 6: Run your search. The overall hiring process begins with a founder screen, then moves on to a deep-dive focusing on the highest-priority focus areas from your gap analysis. Jordan shares a template for the overall hiring process here.
8 Mistakes to Avoid When Hiring a Head of Sales
Finally, keep in mind these eight anti-patterns when hiring a head of sales:
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- Overvaluing big company experience. It’s easy to proxy fit with impressive big company brands and achievements. But a sales leader from Salesforce.com will likely have trouble at an early stage with no brand and no budget.
- Leadership misalignment. If co-founders express dramatically different expectations in the sales needs self-assessment, pause the hiring process. Discuss.
- Skipping gap analysis. Without a gap analysis of your sales engine, you’re shooting in the dark.
- Hiring a VP too early. Hiring a systems-builder before a few good AEs can sell reliably is often disastrous.
- Thinking too long-term. Focus on the next 12-18 months. You can always add an executive down the road.
- Founders not doing initial screening for head of sales. Founders need to screen head of sales candidates themselves.
- Hiring generalist firms. You wouldn’t go to a generic doctor for a specialized surgery, so why do that when it comes to finding your head of sales?
- Fixating on title. Until you’re far up the sales learning curve (and sales manager leveling chart), don’t worry about title; just call it “head of sales.”
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