Companies you'll love to work for

Director, Strategic Finance

Stride Health

Stride Health

Accounting & Finance
Posted on Saturday, November 18, 2023

Stride enables independent workers to reap the benefits of their independence. We simplify the challenges of being self-employed by helping workers handle the complexities of insurance, finances, and taxes — in one convenient platform. Since we were founded in 2014, we have helped over 3.7 million workers save an estimated $5.4 billion on their taxes and monthly health insurance premiums.

Stride partners with over 100 leading companies like Uber, Amazon, DoorDash, and Instacart to provide their independent workers with access to our benefits platform. The company is backed by $96 million in capital from Venrock, New Enterprise Associates, Fidelity’s F-Prime Capital Partners, Mastercard, Allstate and King River.

Cash compensation range: $204,000 - $225,000 USD annually + equity

As our benefits platform gains more traction and continues to grow, so too does the complexity of our financials and the need for greater insight into the levers of our growth. You will be reporting directly to the COO and will work closely with our executive team and board. We’re looking for a deeply strategic finance talent ready to influence at the highest levels of a fast-growth startup. You’ll create the financial, analytical and reporting tissue that supports and propels an aggressive growth plan, and work closely with our Product and Growth teams to deeply understand the high yield growth levers of our business and align our investments behind them. Further below is an example timeline of your first year at Stride.

Within 1 month you’ll…

  • Meet the executive team and leaders across the organization, and being building strong relationships with them
  • Dive into our financial model, understand the levers of growth, update the model, and take stock of current finance and accounting operations and practices
  • Work with the COO to develop an initial set of analyses on key growth levers of Stride’s core business lines
  • Immerse yourself in our strategic planning process, how that drives company decision making, and the large role Strategic Finance will play in driving that process forward
  • Drive the development of Strategic Finance’s next set of leadership goals and objectives

Within 3 months you’ll…

  • Fully own our financial planning and forecasting process, including identifying areas for improvement and refinement, and deeper integration with our accounting systems
  • Be a finance business partner across Sales, Marketing, Product, Engineering and Operations on short-term and long-term strategies, including budget creation and management, modeling and strategic analysis, KPI creation and tracking
  • Build right-sized financial models from scratch to enable business planning and strategic decision making
  • Collaborate with the Controller and our accounting team to model and manage the working capital needs of the business
  • Prepare and deliver timely financial, operational and KPI reporting to executive team and business leaders
  • Facilitate and educate leadership on our financial performance, preparing them for board and investor conversations, and ultimately helping better drive the business

Within 6-12 months you’ll…

  • Lead annual and quarterly budget planning and forecasting cycles, and partner with leaders across the company to resolve competing business priorities
  • Identify and drive initiatives to continuously improve, automate and scale planning, forecasting and reporting
  • Create detailed and integrated financial and operating models to forecast and analyze performance to support and guide both short and long-term strategic plans
  • Develop a forward looking vision for the team, including hiring additional support where needed, identifying the shape of team growth based on forecasted complexity, and key challenges to solve in the future
  • Have contributed meaningfully towards getting the company ready for its next fundraise
  • Feel excited to develop a growth plan for your next 6-12 months at Stride, and looking forward to growing your capabilities and furthering your career!

Experience & Qualifications:

We recognize that underrepresented groups such as women and BIPOC individuals are historically less likely to apply to a role if they don’t meet 100% of the listed qualifications. We encourage you to apply if you meet a majority of the qualifications and this role is aligned with your career trajectory.

When reviewing resumes we’ll be looking to see that you have:

  • Extensive experience within Finance departments, such as FP&A and Strategic Finance.
  • 2+ years of experience [managing strategic finance initiatives] in at least one VC-backed startup (~50-200pp)
  • Successfully led companies in creating and scaling financial and operating models in the past
  • Owned the budgeting and forecasting process

If we have an opportunity to engage you in your interview process, we’ll look to assess that you are:

  • An expert Microsoft Excel user with exceptional analytical skills
  • A phenomenal communicator who has created exceptional partnerships with internal partners
  • Passionate about your craft - we value people who love what they do, and take pride in their work. We want to see that passion in you for understanding the financial mechanics of the business, and delivering value through strong partnership with team leads and our executive team.
  • Able to see the forest for the trees - you have an ability to understand the core levers and economics of our business, how to leverage financial insights to drive financial performance and KPIs, and a keen ability to go from the 2 to the 20,000 ft view.
  • Comfortable with ambiguity - you have a demonstrated ability to operate in a world of unknowns, where you are the expert and exercise appropriate executive judgment, make sound decisions exclusively, and advocate for those decisions effectively.
  • A builder - you are comfortable hiring and scaling teams, implementing new systems and tools, building models and analyses from the ground up, and partnering with our engineering and product teams to drive deeper integrations between our finance systems and operating infrastructure.


Helpful Information:

This resource will help explain Stride’s Compensation Philosophy and compensation practices, and will answer some common questions you might have.

Stride’s Compensation Philosophy utilizes a National Payscale, which is designed to fairly and equitably pay employees based on their performance and impact regardless of geographic location. For employees in the United States, our National Payscale leverages San Francisco Bay Area market data to determine our compensation bands for cash, commissions, or bonus (if applicable) and equity.

Unless otherwise noted, the cash compensation above is the total salary and does not include a bonus. In addition to cash compensation, all full-time Striders will be given stock options to participate in Stride’s equity incentive program. We want all Striders to be an owner of the company, value that ownership, and be able to participate in any future positive outcomes for the company.

Individual compensation packages are based on a few different factors unique to each candidate, including their skills, experience, qualifications, and other job-related reasons. Our compensation ranges are designed to be competitive, equitable, and growth-oriented.

We know that benefits are also an important piece of your total compensation package. To learn more about what’s included in total compensation, check out some of the benefits and perks Stride offers to all US-based employees.

At Stride, we believe in compensating Striders in ways that are true to their value in the marketplace, that inspire and motivate the team to execute our vision, that shape behavior toward productively building and sustaining Stride's culture, and that support the risks and rewards of a fast-growing technology company.

We know the confidence gap and imposter syndrome are a real thing. This can get in the way of meeting incredible candidates, so please don’t hesitate to apply — we’d love to hear from you!

Stride is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.