For Founders

How Startup Founders Can Avoid Hiring The Wrong Early Leaders

Laura Thompson, director of Execs on Deck, shares her insights on how to recruit and retain the right world-class leaders that can take your company to the next level.

 min read
September 29, 2022
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Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders

Note: This article is adapted from a live discussion for the On Deck community featuring On Deck alums Ming Lu and Vik Duggal. If you’re an early-stage founder, angel investor, or exec interested in joining our community, consider applying to one of our programs - you’ll be in great company.

Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders.

Note: This article is adapted from a live discussion for the On Deck community featuring Josefin Graebe. If you’re an early-stage founder, scaling founder, or senior exec interested in joining our community, consider applying to one of our programs.

This article is the first in our annual series Year in Preview.  In the 4 years since we launched the On Deck Founders program, we’ve seen +1000 companies get started and raise over $2B in funding.

Laura Thompson is the program director of Execs on Deck, a curated community of senior leaders looking to accelerate their careers in high-growth startups. Laura is a former founder and ex-Googler, where she launched radical “moonshot” technologies including delivery drones and a smart contact lens while at GoogleX.

In this Q&A, Laura shares how to recruit and retain world-class leaders that can take your company to the next level. 

Too often startups agonize over raising funding and then waste that money hiring the wrong early leaders, so taking proactive steps to approach the right persona with your bold vision is crucial.

By aligning expectations and taking a collaborative approach, recruiting C-suite and VP executives can have an enormous impact on what the culture of innovation looks like at your company. Below, Laura shares frameworks founders can use to set expectations for both sides to work together synergistically, and why a high-growth startup should foster continual growth for top-level executives.

When is the right time to bring an “executive” into your startup? If you’re a founder in the idea stage, is it too early to start courting execs?


World-class founders are amazing at soliciting help early and often. However, I often hear founders say “I haven’t achieved X yet so I’m not ready to talk to senior leaders” or “I just hit Y so we’re kicking off the search for a CMO.” If an arbitrary metric is going to tell you it’s time to bring in a senior leader, you’re going to bring in the wrong person at the wrong time. 

The most successful founders reach out to strong senior leaders continuously (starting at the very beginning of their ideation) and create space for those relationships to play out. Some of the early advisors you reach out to will be one-off conversations, some will become mentors, others may invest, and some may join full-time down the line. Successful startup leadership teams are deeply rooted in trust. The best way to build that kind of trust is to cultivate those relationships over time. 

What do founders most often get wrong in the recruitment process while filling key leadership roles?


Founders often tell me they feel intimidated by and a bit wary of “executives.” They worry an executive will be turned off by how small they are, will point out everything they’ve done wrong, or, worst case, will slow them down by imposing excessive process and bureaucracy. 

Perhaps because of this wariness, I often see founders pitching potential executive hires in wholly uninspiring ways. Rather than falling into the trap of starting your pitch with the brand names of investors or former employers to bolster your legitimacy, lead with your personal motivation and excitement for the problem you’re solving. Your big inspiring vision and early signs of momentum are what’s going to get someone excited to join your team.

Another problem I see regularly is founders using interviews to grill an executive on their functional expertise. Any hire at a VP or C-Suite level is going to have a huge impact on the strategy, culture, and diversity of your company. Making interviews collaborative and soliciting their input on broad business questions like vision, roadmap, and hiring process demonstrate to them that you value the full range of experience they’re bringing to the table. In turn, it also lets them demonstrate to you that they have real value to add to the company’s future. 

How do senior leaders/execs think about compensation when joining an early stage startup?


Execs jumping into startups from bigger companies typically know significantly less about how startup equity works than most founders assume. I often see compensation discussions between founders and early leadership hires stall during the hiring process simply because neither side has enough data to feel confident that they’re getting a good deal. One way around this is to share benchmarked comp data from a database like Pave when you send out an offer. This builds trust (they’re going to Google this anyway) and gives everyone a shared reference point for the conversation that’s based on data, not “perceived worth”.

How should founders be thinking about career development opportunities for senior leaders?


Being a leader at a startup can be an all-consuming role that doesn’t leave a lot of time for networking or thinking through career development. On top of this, it’s far too easy for startups to deprioritize career development for their high-performing leaders when other things are more immediately on fire. Nonetheless, proactively investing in executive development is a “need to have”. Whether it’s hiring an executive coach for your key leaders, sponsoring their participation in a networking group, or just helping that leader carve out time to present at a conference, investing in your leadership team’s growth has a huge ROI.

One of the reasons I started the Execs on Deck community was my own experience making the leap from Google to startups. I suddenly went from being surrounded by peers thinking through similar development challenges to being one of the very few experienced hires in the company. Without support, what could be a steep growth curve can quickly turn into burnout at an early stage startup. It doesn’t help that the career “ladder” looks more like a jungle gym when you move from more traditional companies to the startup world. While there are great programs and networks for founders, I couldn’t find those resources for high-impact leaders at startups, so I created Execs on Deck. 

What is the biggest trend you’re seeing in the startup leadership space right now? 


There has never been a better time for founders to recruit experienced, best-in-class leaders. The unprecedented nature of the past two years has led many people to rethink what is important to them and what they find meaningful. I’m seeing a lot of talented leaders leaving cushy jobs right now because they want space to run. They crave a broader set of responsibilities and the ability to move faster and work more cross-functionally.

This means if you’re a founder building something big and meaningful in the world, it’s an incredible environment to attract seasoned leaders to get behind your vision. The talent pool of experienced execs excited to dive in and help you succeed has never been larger. 

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