Chief of Staff

The opportunity

As Chief of Staff, you will help run the operating system of Holly as we enter our next phase of growth. You will work directly with the founders and leadership team to turn company priorities into execution, with particular ownership across financial planning, company operations, and high-impact cross-functional initiatives.

You will be expected to build systems and take ambiguous problems from definition through execution. At different moments, that could mean rebuilding our company forecast, preparing the board for a major strategic decision, standing up a new business function, or driving an important initiative that does not cleanly 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. While Holly is headquartered in NYC, half the team is based in CA (including Brendan) and you should expect to spend approximately 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
• Communicate with intellectual honesty about what’s working, what’s not, and where we can move faster

Lead our financial planning towards strategic decisions

• Own Holly’s budget, forecasts, and cash plan end to end, partnering with departments to connect resourcing decisions to company growth and priorities.
• Own the analytical foundation for major financial decisions, including headcount planning, scenario analysis, SaaS metrics, and tradeoffs around investment.
• Partner with the founders on investor communications and board reporting, including setting the agenda and preparing materials for effective quarterly meetings.
• Ensure Holly’s financial operations are managed accurately and efficiently, working with vendors and internal teams to understand performance against plan.

Guide Holly's operating system

• Inform and track company-wide KPIs and maintain the systems behind them to keep leadership’s source of truth accurate and timely
• Facilitate 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, including overseeing and developing our People Operations function.
• Support leadership on select external and partner relationships and work closely with Brendan on fundraising and other financing activities as needed.
• Shape company-wide events and initiatives that celebrate wins and strengthen Holly’s culture. 

What you’ll bring

• You have 5+ years of experience, including in consulting, finance, or a similar role at a high-growth startup.
• 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 - $165K + 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.