How To Supercharge Your Startup With Your First Senior Hire

By Julia Austin 

Abigail had just hired Carl as the first head of sales for her fast-growing seed-stage startup. Carl was a seasoned operator who had built sales teams and playbooks for two other startups and was 10 years her senior.

Despite a great interview process and genuine excitement about bringing Carl’s expertise into her startup, she was daunted by the idea that she would be managing someone with so much more experience than her. Abigail’s investors encouraged her to find someone who knew how to lead a sales organization and could take some of the load off her plate so she could focus on other parts of the business such as product and marketing.

But she worried that Carl wouldn’t value her input due to her lack of experience — even though she’s been selling her product since day one — or that he’d exclude her from key strategic decisions that she still wanted to be part of. She wanted to be sure that she set Carl up for success without losing her confidence in her ability to manage him despite their difference in experiences.

I’ve been a senior hire at three different startups and have helped dozens of founders manage their own senior hires. What I’ve learned is that it is critical to have the right mindset and set clear expectations upfront so these more experienced hires can be just the super power you need to scale your venture. Senior leaders can not only take the day-to-day operations of a functional area off your plate, but they can also serve as thought partners and coaches to co-founders and their teams.

Here are two considerations for bringing on first senior hires that can set you up for success.

Your expertise vs. theirs

When I joined DigitalOcean, the founders had reached substantial growth based on their firsthand knowledge of how developers used cloud services. However, they had never scaled engineering and product teams or managed organizations with hundreds of people. As such, they were struggling to ship new features and products at scale.

As their CTO, I brought three key components into the business that most senior hires can offer:

• Domain expertise from my work at Akamai and VMware;
• Team leadership at scale having built and managed teams from zero to 100s of people; and
• Strategic and operational expertise necessary to plan and execute on a a product roadmap.

My domain expertise was important but not as critical as my operational experience in this example. It may, however, be important for another type of hire. For example, an engineering leader who knows how to build great software for a developer tools company, could lack the necessary experience to make a digital healthcare company HIPAA compliant.

So, be sure to think about whether understanding your type of business and customers (the what) is as important as their technical skills (the how). If a candidate has a track record of learning a new type of product or business in the past, this may not matter. However, in some cases, a lack of domain knowledge could impact their credibility with your team and/or external stakeholders. Be thoughtful about whether this matters for each senior hire you make.

Delegation vs. partnership

It can be scary to hand off the management of part of your venture to someone else, let alone someone more experienced than you. So it’s important to find candidates who are willing to invest in a partnership with you and not someone who wants to work autonomously. Even with all the experience and expertise I brought into all of the startups I joined, the founders were still the experts when it came to their business. My job was to help them stabilize their ventures after a huge growth spurt and set them up for success as they approached an IPO. I was their partner and worked very hard to bring them into strategic decisions while mentoring them as they learned to navigate a larger organization.

Your ideal senior hires will be those with a track record of partnering with founders. They know when to bring you into the conversation and are willing to teach you while respecting that you are still the boss. Although you may have delegated important elements of the business to them, ultimately big decisions are still your call. It’s worth noting here that some of the best partnerships like this start with a fractional or trial hire who will give you a sense of what they (and you) are like to work with before coming on board full time.

When searching for these first senior hires, focus on being clear about the problems you are trying to solve and ask candidates how they may go about solving them. If your board has suggested you need more experienced talent, encourage them to articulate what success looks like with that talent on board instead of being prescriptive about a specific job or, worse, pushing a candidate of theirs on you to hire. The more clear your expectations for this role, and the stronger these expectations are communicated to the candidates and your board, the higher the likelihood of success.

Julia Austin is a seasoned operator who has served in leadership roles at several technology startups. She is on the faculty at Harvard Business School and is faculty co-chair of the Arthur Rock Center for Entrepreneurship. As a certified executive coach, Austin works exclusively with startup founders. She is an angel investor, serves on startup boards, and advises many founders through her work with several accelerators. She has three daughters and lives in New York City.

Excerpted with permission from “After the Idea: What It Really Takes to Create and Scale a Startup.” Copyright © 2025 by Julia Austin. Available from Basic Venture, an imprint of Hachette Book Group, Inc.

Illustration: Dom Guzman