Demystifying 'Head of' Hiring

We love advising early-stage Founders on first-in-function hires. Shout out to the team at Hyde Park Venture Partners for inviting us to share lessons learned during a session on ‘Demystifying Head of Hiring’. Here are six takeaways that Magna Sundstrom , Associate Partner & Mandy Edmund , COO shared from their experience placing hundreds of ‘Head of’ roles over the years.

You can hear the full session here.?

What Makes a ‘Head of’?

• They are a player/coach - they are strategic, yet remain very hands-on.?
• They have enough experience to see around corners - ~18 months down the line. This timeline is purposeful as your business should look notably different in 18 months. This leader may be ready to level up into VP or benefit from the leadership of a VP.?
• They have experienced the challenges and uncertainty of scaling an early-stage or high- -growth company in a strategic IC or leadership role and are excited (or crazy enough! ??) to want to do it again. They are hungry for more.?

Don’t Skimp on Upfront Work

• Take the time to define leveling and experience.
• Why is this important? So that the hire can drive the impact that you need.?
• How to do it? “Head of” is an ambiguous title that can range from Sr. Manager to sitting VP. Ask yourself the following questions:

1. What do they need to accomplish in the next 18-24 months?
2. Will they inherit a team?
3. How well do I know this function? Do I need them to see around corners for me?
4. Do I have the bandwidth to manage them?

Founder/CEO self-awareness is one of the greatest tools you can use in hiring. Be honest with yourself and seek the leveling and experience you need to increase your own velocity in other areas of the business.?

When to Hire? Consider the Function

When to bring on a ‘Head of’ depends on the function they will be leading.?

• First GTM Leader - Think about the product, the buyer, and the sales motion, and look for a profile that brings expertise in those areas. This may need to happen as early as Seed and largely depends on the Founder/Co-Founder skill set.
• First Head of People - Necessary at ~30-40 employees. Think about how you will scale your product and whether you need to build culture or heavily recruit. North of 40 people without someone leading the function is where we see (entirely avoidable) HR-related mistakes.
• First Head of Finance - Tricky hire that is historically Series B/C. It’s difficult to find someone who both understands the function and the early-stage startup space. Consider hiring earlier if your product requires or is involved in financing (think mortgage-tech) or has a large inventory overhead.
• First Head of Product - Similar to the first GTM leader, the timing for this role largely depends on the Founder’s skill set and the clarity and conviction they have for the vision of the product. When hiring for this role, be prepared to trust the person to develop the strategy together with you.

(Over)Prepare Your Interview Panel

• But first, prepare yourself. Take the extra calls and talk to your network to calibrate on the ideal profile and your needs.
• Ensure your entire team is clear on the why and expectations of this hire. You could lose even the most perfect hire when the interview panel is not aligned and clear in role expectations.
• Like with many things, mistakes are avoidable if the time and thought are put in. This is particularly true with hiring and candidate experience.?
• The above work is time-consuming but necessary and is where a good recruiting partner swoops in to help.

Write. It. Down.

• At SwingSearch, we focus heavily on documentation. We use a North Star, a Mission-Outcomes-Competency document, and a scorecard (at a minimum) to define what is important and get alignment across the team.
• When managing different opinions and interview styles, it’s important to document key decisions and factors in the search and refer back to them as a guide. This includes defining compensation upfront, so make sure to determine your walkaway number.

Once You Think You’re Done, Add 90 Days?

• Closing the candidate is where you can win or lose the placement. You will stand out by providing an excellent experience to an in-demand candidate with multiple options.?
• Prepare onboarding materials in advance and remember the work is not done when the offer has been accepted. The first 90 days of an employee's journey will set the tone, pace, and quality for future work. Check in daily with the hire for the first 2 weeks and weekly after that (at a minimum).

Thanks again to Jim Conti and the Hyde Park Venture Partners team for having us for a lively conversation!