Chief of Staff

The opportunity

As Chief of Staff, you will work directly with the founders and leadership team as Holly enters its next phase of growth, turning company priorities into execution.

Much of the work is ambiguous. You will build the systems it needs and take it from definition through execution. That could mean rebuilding our company forecast, preparing the board for a major strategic decision, standing up a new business function, or driving an initiative that doesn’t belong to any one team.

You will report to Brendan Hellweg, co-founder and Co-CEO, and work closely with both founders and all department heads on strategic projects. Holly is headquartered in NYC, but half the team is based in CA (including Brendan) and you should expect to spend up to one week per month on the West Coast.

What you'll do

Act as a trusted partner to the co-founders and leadership team

• Maintain a rigorous view of progress across company initiatives and surface where we are off track, under-resourced, or avoiding a hard decision, and turn priorities into named owners and goals that get done
• Communicate with intellectual honesty about what’s working, what’s not, and where we can move faster
• Help leadership weigh investment tradeoffs, including headcount and budget, and make the numbers behind them clear enough to decide on
• Prepare board and investor updates and support fundraising

Guide Holly's operating system

• Maintain company-wide KPIs and the systems behind them to keep leadership’s source of truth accurate and timely
• Run quarterly and annual planning across departments to continuously improve Holly’s core operating cadences
• Tie these pieces together with our financial metrics and investor reporting to orient our work towards outcomes

Drive cross-functional projects end to end

• Own high-impact initiatives from definition through execution, working across teams to establish partnerships, build new business functions, and redesign processes
• Fill operational gaps ahead of other hires, such as overseeing and developing our People Operations / Recruiting functions
• Support external partnerships and company culture and recognition

What you’ll bring

• You have 5+ years of experience in consulting, finance, or strategy and operations / product at high growth companies.
• You are an analytical and opinionated communicator with a bias to action, meaning that you seek to understand, convey, and act.
• You handle startup finances, SaaS math, and board presentations with ease.
• You are unusually good at moving between altitude levels. You can debate company strategy in the morning, rebuild a forecast in the afternoon, and personally fix a broken operating process before the day is over.
• You collaborate with empathy and exercise sound judgement over confidential or sensitive information.
• You are passionate about our mission: this will be an unusual job with exceptional upside, but you’ll make it through crunch times knowing you’re empowering public servants to make communities healthier, safer, and more prosperous.

About the interview

• Step 1: Screening Call with Recruiter
• Step 2: Intro Call with Brendan
• Step 3: Take-home assignment & presentation
• Step 4: Onsite interview with the founders

Compensation

• Base Salary: $145K - $175K + equity + bonus

Holly is an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Holly is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.