Level up your team with advisors

How to bring in experts to coach each department

DEAR STAGE 2: We just wrapped up our first board meeting of 2024 and it’s clear we have some gaps in our leadership team heading into the new year. Specifically our Head of Marketing and Head of Product were both promoted internally and are in first-time leadership positions. They are both talented, but lack experience and are growing into their roles. What can we do to bring them up the learning curve as fast as possible? ~INVESTING IN OUR TEAM

DEAR INVESTING IN OUR TEAM: Advisors! Advisors! Advisors! 

As the CEO, you are not expected to have deep functional expertise in every department. You also can’t afford (nor is it the right decision, for many reasons) to hire senior experienced leaders in the early stages of a startup. BUT, you can tap into an incredible amount of knowledge and experience through advisor relationships. 

Most startups have advisors in some capacity, but I usually find that those relationships are held by the CEO. As the CEO, you can move faster by augmenting your team and bringing in experts to coach each department. 

Tips to get you started

• Source the right advisors

  • Define the ideal profile (see below)

  • Ask your network for referrals

  • “Interview” through working sessions with both you and your leader

• Hire no more than 1-2 advisors per leader

  • Too many cooks in the kitchen is not helpful. If content marketing is the #1 priority, find a content marketing expert — you can look for someone with event, product marketing, etc. experience in the future

• Keep the term short (<12 months), and make sure you can cancel at any time

  • As a startup, your needs change quickly — the advisor who is right for today probably won’t be in the future.

• Set clear goals you are working towards

  • Write them down, check in on them, hold the advisor accountable

• Define a time commitment and operating rhythm

  • Ex: quarterly goal setting call with CEO, weekly coaching call with leader, monthly written recap on progress to CEO

• Consider bringing your advisors together

  • Each advisor has blinders on — they see only a small part of your business through the lens of the leader they work with. With this in mind, consider bringing all of your advisors together to share their observations, and use this time to share priorities for the coming period. Doing this the week before each board meeting can give you some great perspective!

Selection guidelines

Profile is always the hardest part. While you obviously need to tweak these for your unique needs, I wanted to share some ideas on what’s most important to each function to get your started:

• Sales: Go senior here. You’re looking for someone who can help set strategy, see a few steps ahead, and coach up your leader. It’s critical that this person has run sales teams with a similar demand generation strategy and GTM motion, but does not claim to have “the playbook” — they need to be ready to bring their experience and apply it to your unique company and situation.

• Marketing: Look for current active skill sets — people who have successfully operated at your stage in the last 3-5 years. Marketing is a likely candidate for multiple advisors to supplement your team based on needs (brand, demand gen, product marketing, etc…).

• Customer Success: Focus on finding broad experience — someone who has overseen onboarding, renewals, support, etc… and can give guidance on how this function builds out over time, including KPIs and hiring profiles.

• Product-Led Growth (PLG): This is still a relatively new discipline, but certain companies have excelled. This is the most critical advisor to a PLG business — go big. Target someone who worked the early days of a very successful company you admire. Pedigree matters.

• Product: We recommend seeking out a product leader who has experience with 1) your end user/end market and 2) a similar GTM motion and user journey (e.g. don’t bring on an advisor with 20 years of enterprise application experience if you are developing an open source product for developers).

• Engineering: There are 2 flavors here and it comes down to your technical leader. Either look for someone who can coach the founding CTO to hire in the VPE. Or, look for someone who can help the founding CTO grow as a people manager, develop the team, and build scalable practices.

• People: This is potentially the most-overlooked role in an early business, which is ironic given early-stage companies need to hire and onboard many roles on a tight timeline. Often, the early hire in People Operations comes from recruiting, and would benefit from a senior advisor who can tackle questions spanning everything from culture and team building, to compensation benchmarking, to compliance. 

• Finance & Operations: Fractional or outsourced finance functions tend to be common in the early stages of a business. However, as soon as you bring the function in house, this advisor can be really helpful in thinking through some of the nuances of reporting, fundraising, modeling and cash management. 

It’s never too early to start assembling your advisory team. This group should grow and change along with your business — always be on the look out for the person who can help you get to the next level.

Until next week!