Chief of Staff

Holly•New York, NY

16h•$145,000 - $165,000•Hybrid

About The Position

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.

Requirements

5+ years of experience, including in consulting, finance, or a similar role at a high-growth startup.
Analytical and opinionated communicator with a bias to action, meaning that you seek to understand, convey, and act.
Handle startup finances, SaaS math, and board presentations with ease.
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.
Collaborate with empathy and exercise sound judgement over confidential or sensitive information.
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.

Responsibilities

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.