About this role

Reporting to the SVP, FP&A - serve as a strategic business partner to executive leadership, shaping financial strategy and providing forward-looking, data-driven insights to guide decision-making and resource allocation.
Lead the entire corporate financial planning process, including annual budgeting, rolling forecasts, long-range planning, and scenario modeling.
Drive automation and systems optimization to deliver operational excellence across FP&A activities.
Champion auditability, transparency, and investor readiness
Please note that this role will be based in Chicago and will follow a hybrid office schedule

What you’ll do

Lead development of the annual operating plan, monthly forecasts, and long-range models (P&L, cash flow, balance sheet, KPI tracking).
Conduct deep variance analysis and trend forecasting; deliver high-impact insights to executives and board members.
Build and maintain robust, scalable models—covering unit economics, ROI evaluations, product/channel-level financials, cost optimization, and capital allocation recommendations.
Streamline and automate financial planning processes using tools like Pigment/Adaptive, NetSuite, or Excel—improving speed, accuracy, and self-service reporting capabilities.
Prepare executive-level materials, including board reports, quarterly investor reporting, and EAC BvAs/FvAs—ensuring clarity and strategic alignment.
Partner cross-functionally with Accounting, HR/People Ops (e.g., headcount planning, benefits), Legal, and Corporate Development.
Lead, mentor, and scale a high-performing, world-class FP&A team across functions or geographies.
Drive strategic ad hoc initiatives—like business case evaluations, or project investments—to support corporate strategy and capital allocation.

What we’re looking for

13+ years of progressive experience in strategic finance/FP&A roles, including at least 5 years in leadership over corporate FP&A within high-growth or public environments.
Demonstrated success in optimizing planning cycles, implementing financial systems, and driving process excellence.
Advanced skills in financial modeling, scenario planning, KPI development, and strategic performance analysis.
Excellent communication and storytelling capabilities to present complex financial information to executives, boards, and investors.
Proven experience building, coaching, and retaining top-tier remote FP&A talent.
Hands-on user of financial planning tools and systems (e.g., Anaplan, Pigment, Adaptive Planning, NetSuite, Excel).
Agile, growth-oriented mindset—able to thrive in dynamic environments and drive scalable processes from the ground up.
Bachelor’s degree in Finance, Accounting, Economics, or a related field; MBA or advanced finance-related degree strongly preferred.

Nice to have

Experience in the digital healthcare sector; B2B and D2C business models
Experience with M&A and integrations
Comfort with public company financial processes—forecasting, external reporting, IPO readiness, earnings guidance, and investor engagement.

As a remote position, the salary range for this role is:

$180,000—$220,000 USD

Who we are

Transcarent and Accolade have come together to create the One Place for Health and Care, the leading personalized health and care experience that delivers unmatched choice, quality, and outcomes. Transcarent’s AI-powered WayFinding, comprehensive Care Experiences – Cancer Care, Surgery Care, Weight – and Pharmacy Benefits offerings combined with Accolade’s health advocacy, expert medical opinion, and primary care, allows us to meet people wherever they are on their health and care journey. Together, more than 20 million people have access to the combined company’s offerings. Employers, health plans, and leading point solutions rely on us to provide trusted information, increase access, and deliver care.

We are looking for teammates to join us in building our company, culture, and Member experience who:

Put people first, and make decisions with the Member’s best interests in mind
Are active learners, constantly looking to improve and grow
Are driven by our mission to measurably improve health and care each day
Bring the energy needed to transform health and care, and move and adapt rapidly
Are laser focused on delivering results for Members, and proactively problem solving to get there

Total Rewards

Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity.

Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options.

Our benefits and perks programs include, but are not limited to:

Competitive medical, dental, and vision coverage
Competitive 401(k) Plan with a generous company match
Flexible Time Off/Paid Time Off, 12 paid holidays
Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance
Mental Health and Wellness benefits

Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out!

Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences.

Sr. Director, Corporate FP&A

About this role

Requirements

Nice to have

Benefits

About Transcarent