Chief of Staff

Holly is setting the standard in government technology because we empower the right people to serve a vital and shared mission. We believe the only way to achieve our mission is to build an exceptional business. This work depends on our values:

• Lead with trust: You will own your work from day one.
• Learn by doing: You will be a student and an entrepreneur.
• Serve with purpose: You will put public servants and their outcomes first.
• Move with conviction: You will guide big decisions, fast.

• →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

• 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.

• 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

• 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 - $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.