Sr. Director, People Operations & Total Rewards

Betterment; New York (NY); Hybrid; USD 200,000 - 225,000; Full time

Benefits offered by this job

Medical, dental and vision coverage

Equity for all employees

Flexible PTO and sabbatical

401(k) match and student loan match

Professional coaching

Job summary

Betterment, a NYC-headquartered, technology-driven financial services company, seeks a Senior Director of People Operations & Total Rewards to shape and execute a holistic compensation strategy and oversee payroll, benefits, and related HR systems. You will design scalable frameworks to attract, retain, and motivate talent while ensuring compliance and financial discipline.

You’ll partner with the CPO, CFO, and executive team to align total rewards with company goals and drive data-driven

Qualifications

• 10+ years of progressive experience in People Operations and Total Rewards, with leadership experience.
• Deep knowledge of payroll, benefits, and employment laws, practices and systems.
• Proven ability to lead People Operations teams in high-growth environments.
• Experience managing HR systems (e.g., ADP, Pave, CultureAmp, Lattice, Greenhouse) and driving data accuracy and compliance.
• Strong project management and scalable systems design skills, including IPO readiness.
• Collaborative, proactive, and detail-oriented with a bias to action.

Responsibilities

• Design, implement, and govern compensation structures and total rewards programs.
• Lead market benchmarking, pay equity analyses, and compensation reviews.
• Partner with CPO and CFO on strategy, budgeting, and long-term incentive planning.
• Collaborate with Finance to align policies and forecast compensation costs.
• Oversee benefits programs and ensure regulatory compliance (ERISA, ACA, HIPAA, FLSA).
• Manage relationships with benefits providers and HR vendors to optimize cost and experience.
• Lead payroll function to ensure accuracy and timely cycles.

Skills

People Operations

Total Rewards

Payroll management

HR systems

Data-driven decisions

Cross-functional leadership

Tools

ADP

Pave

Culture Amp

Lattice

Greenhouse

Job description

About Betterment

Betterment is a leading, technology-driven financial services company that offers investing, savings and retirement solutions for retail investors and investment advisors as well as financial wellness solutions, including a 401(k) for small and medium-sized businesses. Our team is passionate about our mission, to empower people to build wealth with confidence and ease. We’re headquartered in NYC and offer hybrid NY-based positions (four days/ week in-office, with no required office days during the summer and winter holidays).

About Betterment

Betterment is a leading, technology-driven financial services company that offers investing, savings and retirement solutions for retail investors and investment advisors as well as financial wellness solutions, including a 401(k) for small and medium-sized businesses. Our team is passionate about our mission, to empower people to build wealth with confidence and ease. We’re headquartered in NYC and offer hybrid NY-based positions (four days/ week in-office, with no required office days during the summer and winter holidays).

About The Role

As Senior Director of People Operations & Total Rewards, you’ll shape and execute a holistic compensation strategy that’s both strategic and operational. You’ll lead all aspects of People Operations & Total Rewards (e.g., compensation, equity, payroll, benefits, and related-HR systems), ensuring programs are data-driven, competitive, and aligned with our company mission. As a trusted advisor to the CPO, CFO, and executive leadership team, you will play a critical role in designing and executing total rewards strategies that attract, retain, and motivate talent, while ensuring scalability, compliance, and financial discipline. You’ll act as both architect and operator: designing scalable frameworks while staying close to the details that make them work. This role is based out of our NYC office. For jobs based out of our NYC HQ, we require in office attendance Monday through Thursday, weekly. Below we’ve reflected the base salary range we would offer for this position. Actual salaries may vary depending on factors including but not limited to location, experience, and performance. The range listed is just one component of Betterment’s total compensation package for employees.

• New York City: $200,000 - $225,000

This job may also be eligible for variable compensation in the form of a company incentive bonus.

A day in the life

• Design, implement, and govern compensation structures, including frameworks, pay band architecture as well as supporting equity programs and incentive plans
• Lead market benchmarking, pay equity analyses, and compensation reviews to ensure competitiveness, fairness, and transparency
• Partner with the CPO and CFO on compensation strategy, annual budgeting, and long-term incentive planning
• Collaborate with the Finance team to align policies and reporting across functions, as well as forecast compensation costs in support of workforce planning
• Manage and continuously improve benefits programs and ensure compliance with employment and benefits regulations (ERISA, ACA, HIPAA, FLSA, and others)
• Cultivate strong relationships with benefits providers, brokers, and HR technology vendors to optimize cost, service, and employee experience
• Lead the payroll function, ensuring compliant, accurate, and timely payroll cycles
• Partner cross-functionally with Finance, Legal, and external vendors to ensure compliance with complex tax and employment laws, while continuously improving payroll systems and processes
• Own HRIS and people data infrastructure-ensuring accuracy, reporting, and actionable analytics
• Drive operational excellence across People Operations, ensuring smooth execution of payroll, onboarding/offboarding, and compliance practices

What We’re Looking For

• 10+ years of progressive experience in People Operations and Total Rewards, with at least 5 years in a leadership capacity
• Deep knowledge of payroll, benefits, and employment laws, practices and systems
• Proven ability to lead People Operations teams in high-growth environments
• Experience managing HR systems (e.g., ADP, Pave, CultureAmp, Lattice, Greenhouse) and driving data accuracy and compliance
• Strong project management and process design skills, particularly around building systems that scale with business growth (including IPO readiness)
• A collaborative, proactive, and detail-oriented approach with a passion for operational excellence and a bias to action

Join a team built on these core values

We change lives

Be a part of a community of innovators working to transform financial outcomes for real people. Your work will make an impact, always laddering up to our mission; to empower people to build wealth with confidence and ease.

We set audacious goals

We set them for the company, our customers, and ourselves, and we won’t stop until we reach them. We don’t just show up; we give our all, then celebrate our wins.

We value all perspectives

When we collaborate, we're at our best. We believe diverse perspectives lead to better outcomes and strive to uphold our supportive and inclusive community.

We simplify financial services

We’re financial services pioneers, always finding new ways to improve, optimize, and enhance. Constant improvement is in our DNA.

Our Commitment To Your Total Well-being

• We offer a competitive suite of benefits, including medical, dental, and vision coverage; life and AD&D insurance; short- and long-term disability; infertility support and WPATH-aligned transgender health benefits; an Employee Assistance Program (EAP); transit benefits and FSA and HSA options
• Ownership: Equity for all employees, including new hire and refresher grants.
• Time: Flexible paid time off, paid parental leave, and a fully paid four-week sabbatical in your sixth year.
• Growth: Company-paid professional coaching for all employees.
• Wealth: Day-one 401(k) match plus matching on qualified student loan payments.

What Happens Next

We’ll take a few weeks to review all applications. If we’d like to spend more time with you, we’ll reach out to arrange next steps, which will include 3-4 sets of meetings with your future colleagues. In the interview process, we’ll look to learn more about your skills, experiences, capabilities, and motivators. Many of our questions will be aimed at understanding how you might operate here at Betterment. Depending on the role, we may ask you to complete a case study exercise or technical assessments, as we want to collect a robust set of data points to better inform our decisions. On average, it takes us around 3-5 weeks to make a hiring decision, depending on your availability and sense of urgency. As a best practice, we aim to interview at least 2-3 final round candidates before making a hiring decision. Please note that, as we usually receive an overwhelming number of applications for open positions, we’re unable to offer individual feedback during the interview process. We recognize that interviewing for a new role is a big deal. We appreciate you considering Betterment as the next step in your career, and our Recruiting Team is here to support and advocate for you through the interview process!

Betterment is dedicated to providing accommodations to candidates upon request. If you need accommodations at any point throughout the interview process, please reach out to your recruiter.

Please note that in any materials you submit, you may redact or remove age-identifying information such as age, date of birth, or dates of school attendance or graduation. You will not be penalized for redacting or removing this information.

Come join us!

We’re an equal opportunity employer and comply with all applicable federal, state, and local fair employment practices laws. We strictly prohibit and do not tolerate discrimination against employees, applicants, or any other covered persons because of race, color, religion, creed, national origin or ancestry, ethnicity, sex, gender (including gender nonconformity and status as a transgender or transsexual individual), sexual orientation, marital status, age, physical or mental disability, citizenship, past, current or prospective service in the uniformed services, predisposing genetic characteristic, domestic violence victim status, arrest records, or any other characteristic protected under applicable federal, state or local law.