VP of Strategic Finance


We have a 4 day work week (32hrs) - every Friday is off!

Posted 5 days ago

⚠️ You'll be automatically rejected if you can't work from USA

We strongly encourage people of color, lesbian, gay, bisexual, transgender, queer, and non-binary people, veterans, parents, and individuals with disabilities to apply. Real is an equal opportunity employer and welcomes everyone to our team. If you need reasonable adjustments at any point in the application or interview process, please let us know.

In your application, please feel free to note which pronouns you use (For example - she/her/hers, he/him/his, they/them/theirs, etc).

We Are Real.

Real is a venture-backed mental health care company based in New York City. We’re a team of innovators, clinicians, and technologists on a mission to make caring for our mental health a priority. We're redesigning mental healthcare through a digital platform and in-person experience, integrating empathy, design, and progressive care to build the most elevated end-to-end mental healthcare experience, while also improving the quality of care itself. We’re not simply “normalizing” mental health care, we’re celebrating it.

We’re looking for a VP of Finance & Strategy who is passionate about mental wellness.

The VP of Finance & Strategy will report to our Chief Executive Officer and contribute to the company’s growth by partnering with our executive team to provide in-depth financial management, analysis, and strategic insights to manage the runway and drive our growth of the business. We are looking for someone highly analytical with experience in B2B businesses and digital subscription models to accurately track performance trends and identify growth opportunities.

The ideal candidate has multiple years of experience building and leading finance and strategy teams at a venture-backed digital subscription, B2B company.

The company is based in NYC, though the role is remote.

A day in the life:

  • Build, improve and maintain the company model and operating plan, linking key actions and inputs to company growth and profitability
  • Translate market intelligence, business trends, and member insights into every aspect of Real's growth strategy, inclusive of distribution channels, audience segments, and new product lines. This individual will research and define recommendations from where and how we launch, to what products we roll out, and how we bring those products to the market.
  • Run the complete budget cycle, from budgeting and planning to decision-making on spending and variance analysis
  • Work with the company executives to steer financial analyses around key decisions
  • Provide in-depth financial management, analysis, and strategic insights to executive leadership team, maximizing runway
  • Evaluate, advise and analyze the impact of short and long-term planning and implementation of new strategies- develop financial models to help inform strategic decisions and evaluate LTV, ROI, and other financial metrics
  • Lead, build and manage the finance and business operations function including BizOps, FP&A, Accounting, and Legal - the role will be both tactical and strategic
  • Partner with CEO & leadership team to strategize and prepare relevant financial statements/reports for subsequent rounds of fundraising
  • Assist with investor relations, including crafting board communications and fundraising materials
  • Partner with Employer Sales team in developing B2B pricing framework, and identifying insights to improve sales engine
  • Partner with Consumer Partnerships team in identifying insights to improve consumer partnerships ROI
  • Partner with People team in developing compensation and total rewards strategies

You’ve got:

  • 15+ years in finance and/or strategy
  • 10-12 years experience leading and building finance and strategy teams
  • 4+ years experience in investment banking and/or management consulting
  • Experience leading finance or business operations for a B2B digital subscription company
  • Experience working with venture-backed companies
  • Experience and excitement to build finance infrastructure from the ground up, from the strategic to the tactical
  • Ability to translate your financial chops about the human impact of our work
  • A track record for hiring, building, and managing a finance team
  • A strong sense of collaboration & communication and prior experience working with leadership
  • Exemplary verbal and written communication skills

We're extra stoked if you:

  • Have experience owning finance in a content business
The base salary for this role is between $185,000 and $245,000, depending on skill set and experience level. Our compensation program is geographically-neutral, meaning that we do not adjust our pay ranges based on where you live, so this salary range applies to all candidates.

You are:

Passionate about mental wellness

  • You’re excited to improve mental healthcare and expand the number of people who have access to it.
  • You know the wellness market.
  • You care about the well-being of others.

Excited to build something from the ground up

  • You thrive in a fast-paced, scrappy start-up environment.
  • You’re not afraid to roll up your sleeves to get the job done.
  • You’re a self-starter; you don’t need instructions to get work done.


  • You pull insights from data, ensuring new ideas come from member experience and utilization
  • You seek data and know how to collect more of it when needed
  • You are excited to receive feedback and grow

A team player

  • You know it takes a village.

We’re committed to your health and happiness (...which are synonymous, you know).

When deciding what benefits should look like at Real, we started by thinking long and hard about what employees need not only to work well, but to live well. Benefits impact how we act, rest, grieve, set boundaries, and take care of ourselves and others — and that means quality benefits are a fundamental part of not just a mentally well company, but a mentally well society. At Real, we want to offer our employees more than just "permission" to occasionally take a vacation or comp a therapy session. We want to give them the support and autonomy they need to feel well and maintain full lives outside of work.


  • Competitive salary, plus equity in an early-stage startup. Emphasis on “plus”—we won’t use equity to low-ball you.

Healthcare for Full-Time Employees:

  • 100% company-funded health, vision, and dental insurance. That means no monthly premiums coming out of your paycheck.
  • FSA plans
  • Free One Medical membership
  • Free Real membership
  • $1800 annual mental wellness stipend you can put toward therapy, psychiatry, fitness and other wellness services
  • Short- and long-term disability coverage
  • Life insurance

Retirement for Full-Time Employees

  • 401(k) — we don’t match yet, but you’ll thank us for the compound interest later.


  • Unlimited PTO…that we actually encourage you to take, we promise.


  • Four day work weeks Monday-Thursday
  • Four-week paid sabbatical after five continuous years of work at Real.

Floating Holidays

  • Three floating holidays in addition to company-wide federal holidays so you can celebrate what’s important to you.

Grief Break

  • Real employees receive two weeks of paid time off in the event of losing a loved one. We know grief doesn’t have an end date, and we also know that “unlimited PTO” isn’t enough for most people to actually take ample time away from work. We want to support the process of grieving by naming this, and offering employees the opportunity to grieve without thinking of work.


  • Competitive paid parental leave and flexible return to work policy.


  • Flexible working environment — if you want to exercise at three PM, go for it.
  • Remote-inclusive team — whether you work from Colorado or NYC, you’re 100% part of the team.
  • Autonomous work culture. We don’t have to see a green dot on Slack to trust that you’re doing your job.

Growth at Work

  • We invest in your career. Our company's growing quickly, and we'll give you the opportunity to do the same. You'll have access to a number of professional development opportunities so that you can keep up with the company's evolving needs and grow your career along the way.

The responsibilities and duties of this position described here are representative of those an employee must perform. This is not a comprehensive list and other duties may be assigned.

We are an Equal Employment Opportunity ("EEO") Employer. It has been and will continue to be a fundamental policy of Real not to discriminate based on race, color, creed, religion, gender, gender identity, pregnancy, marital status, partnership status, domestic violence victim status, sexual orientation, age, national origin, alienage or citizenship status, veteran or military status, disability, medical condition, genetic information, caregiver status, unemployment status or any other characteristic prohibited by federal, state and/or local laws. This policy applies to all aspects of employment, including hiring, promotion, demotion, compensation, training, working conditions, transfer, job assignments, benefits, layoff, and termination.

For your safety, we want you to be aware that unauthorized individuals claiming to be Real employees are extending false employment offers to steal money and personal information from job seekers. They are using legitimate websites and social media platforms and may use an unauthorized Real logo and employee name. Do not engage if you believe communication is fraudulent.

Real employees communicate using email addresses that end with @join-real.com.

Real will never request money or credit card information or ask for personal details like address, social security number, bank information, or tax documents early in the interview process.

If you suspect you’ve encountered an instance of recruitment fraud:

  • To report a suspicious email or job ad, [email protected] and include as much detail as possible (any documentation will assist us).
  • Report the email address as “Phishing” through your email provider. This will help get the email account shut down.
  • If you believe you have been a victim of online recruitment fraud, contact the FBI’s Internet Crime Complaint Center at ic3.gov

Real takes this very seriously and we hope by sharing this information we can prevent potential jobseekers from interacting with these scams.


Where you go to feel.

Our Working Week

We have a 4 day work week (32hrs) - every Friday is off!

  • Mon
  • Tue
  • Wed
  • Thu
  • 🏖️

Our Vacation Policy

We have an unlimited vacation policy (we encourage people to take up to 8 days per quarter)

  • 32 days
  • 52 Fridays
  • 84 days off per year

Our Remote Working Policy

We are remote first but we also have an office in NYC.

Our Employee Benefits

  • Health insurance
  • 401(k)
  • Transparent Salaries
  • Flexible working hours
  • Generous parental leave
  • Dentalcare
  • Childcare support
  • Equipment allowance
  • Life & Disability Insurance
  • Opportunties for Sabbaticals
  • Mental Health Support

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