Sarah Liebel – CEO of Nayya

Sarah Liebel is the CEO of Nayya, an AI-powered benefits intelligence and orchestration platform helping employees make better decisions about healthcare, insurance, retirement, and financial benefits.

A veteran technology executive with more than two decades of experience scaling high-growth companies, Liebel has held senior leadership positions at Groupon, BetterUp, and 1stDibs. She joined Nayya in late 2024 as President and Chief Operating Officer before becoming CEO on January 1, 2026.

Under Liebel's leadership, Nayya is pursuing a broader vision: using AI and benefits intelligence to simplify some of the most complicated and consequential financial and healthcare decisions people make throughout their lives.

In 2025, Nayya generated more than $30 million in revenue and reached nearly one million users, while the company also acquired fintech startup Northstar to expand into financial-advisory and wealth-management use cases.

Who Is Sarah Liebel?

Sarah Liebel is a technology executive, board member, operator, and the current CEO of Nayya.

Her career has focused on building and scaling technology companies across consumer internet, enterprise software, digital health, and fintech.

Unlike many startup CEOs who come directly from engineering or founding backgrounds, Liebel is primarily an operator and growth executive.

She has experience taking companies through multiple stages of development—from early growth through major liquidity events and public markets.

That operating experience is now central to her role at Nayya.

Her stated mission is particularly focused on making complicated health and financial decisions easier for people to understand and act upon. The Conference Board describes her as passionate about democratizing access to information and building intelligent systems that empower people to make confident decisions in complex moments.

Education

Liebel holds a bachelor's degree from Tulane University and an MBA from Northwestern University's Kellogg School of Management.

She is also a member of the Kauffman Fellows Program, an influential network focused on venture capital and technology entrepreneurship.

Her education combines liberal-arts and business training with the operating experience she subsequently developed across several high-growth technology companies.

Starting Her Technology Career

Liebel's professional career developed during the rapid expansion of consumer internet companies.

Rather than remaining in a single industry, she moved across several technology categories, developing expertise in:

• Product growth
• Go-to-market strategy
• Revenue generation
• Consumer products
• Enterprise partnerships
• Operations
• Strategic alliances
• Company scaling

This cross-functional experience eventually positioned her to take senior operating roles at some of the most recognizable technology companies of the 2010s and 2020s.

Groupon and the Early Startup Era

One of the most important chapters of Liebel's career was her time at Groupon.

She joined Groupon during its high-growth period and became one of the company's early executives.

Liebel remained with the company through its transformation into a major publicly traded technology company and its 2011 IPO.

Her Groupon experience exposed her to one of the most difficult challenges facing startup executives: how to maintain growth and organizational execution while moving from a rapidly expanding private company into the public markets.

That experience would later become valuable in her work with other high-growth technology businesses.

1stDibs

Liebel later joined 1stDibs, the luxury e-commerce marketplace.

She ultimately served as the company's Chief Revenue Officer and helped lead the business through its transition toward the public markets.

1stDibs eventually went public in 2021.

The experience gave Liebel additional exposure to marketplace economics, revenue operations, consumer behavior, and public-company management.

It also reinforced a recurring theme in her career: joining technology companies during important inflection points and helping build the systems necessary for their next stage of growth.

BetterUp

Before joining Nayya, Liebel became President and Chief Growth Officer at BetterUp, the digital coaching and leadership-development company.

BetterUp works with enterprises and HR leaders to improve employee performance, engagement, leadership, and wellbeing.

At BetterUp, Liebel was responsible for areas including:

• Sales
• Go-to-market
• Product growth
• Strategic alliances
• Consumer products

Her role gave her significant experience operating at the intersection of technology, employee benefits, workplace wellbeing, and enterprise HR.

Those areas would become directly relevant to her next chapter at Nayya.

Joining Nayya

Liebel joined Nayya in late 2024 as the company's first-ever President and Chief Operating Officer.

The appointment represented a major expansion of Nayya's leadership capabilities.

At Nayya, she initially took responsibility for a broad range of functions, including:

• Product
• Technology
• Finance
• Go-to-market
• Operations

Nayya announced her appointment in October 2024, describing Liebel as an executive with more than 20 years of experience scaling leading technology companies.

Rather than arriving simply as a sales or growth executive, Liebel took on a company-wide operating role.

Becoming CEO of Nayya

On January 1, 2026, Liebel became Nayya's CEO.

The transition was part of a planned succession process that began in 2024.

Nayya founder Sina Chehrazi, who had served as CEO since the company's founding, moved into the role of Executive Chairman.

Chehrazi said the transition followed more than a year of Liebel driving significant impact across the company. He highlighted Nayya's growth to more than four million lives served, more than 65% growth in 2025, and its progress toward profitability.

The leadership transition is important because it places an experienced scale-up operator at the helm of Nayya as the company moves into its next phase.

What Is Nayya?

Nayya is a benefits intelligence and orchestration platform.

The company uses data, artificial intelligence, and personalization to help people navigate complex employee benefits.

Its technology is designed to help employees understand and make decisions involving:

• Health insurance
• Supplemental insurance
• Retirement
• 401(k) plans
• Healthcare spending
• Financial benefits
• Claims
• Employee benefits utilization

For employers, Nayya provides technology designed to improve employee engagement with benefits while reducing the complexity surrounding benefits administration and decision-making.

The company's broader vision is to turn fragmented benefits information into personalized guidance.

The Problem Nayya Is Solving

Healthcare and employee benefits are notoriously difficult for consumers to understand.

Employees may have dozens of plan options, complex deductibles, networks, copay structures, exclusions, tax considerations, retirement options, and other financial decisions to navigate.

The problem is not simply a lack of information.

There is often too much information.

Nayya's proposition is that AI can translate that complexity into personalized recommendations.

Instead of requiring an employee to become an expert in health insurance, the platform can analyze their circumstances and help them understand which options may make the most sense.

That is the core idea behind Nayya's benefits-intelligence platform.

Nayya's AI Strategy

AI is central to Liebel's vision for Nayya.

But she has emphasized that healthcare and financial benefits are different from lower-risk applications of AI.

If an AI system makes a bad recommendation about a restaurant or email, the consequences may be minor.

If an AI system gives poor guidance about health insurance or retirement savings, the consequences can be significant.

Liebel has therefore argued that AI in benefits requires a higher standard of accuracy, trust, transparency, and personalization.

In an April 2026 article, Liebel highlighted examples where an incorrect recommendation could affect a family's healthcare costs, an employee's use of an HSA, or a retiree's retirement contributions.

Her philosophy is that AI should not simply make benefits software faster.

It should make the decision-making process safer and more understandable.

The Agentic Benefits Adviser

Nayya has been moving toward what it describes as agentic AI for employee benefits.

In 2025, the company launched an AI-powered benefits adviser capable of providing tailored guidance to employees.

This represents a shift from traditional benefits software.

Instead of users navigating a series of menus and documents, an AI system can potentially understand the user's circumstances and help them identify appropriate options.

The long-term vision is an intelligent benefits assistant that can remain available throughout the year—not just during annual open enrollment.

Beyond Open Enrollment

Traditional employee benefits technology often focuses heavily on open enrollment.

That is when employees choose health insurance and other benefits for the coming year.

But financial and healthcare decisions occur throughout the year.

Employees may:

• Have a child
• Get married
• Change jobs
• Become seriously ill
• Need surgery
• Change their financial circumstances
• Begin saving for retirement
• Need to submit a healthcare claim

Liebel's vision for Nayya extends beyond annual enrollment.

The company wants benefits intelligence to become a continuous service that helps employees make better decisions whenever important life events occur.

The Northstar Acquisition

One of Liebel's most significant early achievements at Nayya was helping lead the company's acquisition of Northstar, a fintech focused on employee financial wellness.

The acquisition expanded Nayya beyond healthcare benefits into broader financial wellbeing and financial-advisory use cases.

For Nayya, the strategic logic was straightforward.

Health and financial decisions are increasingly interconnected.

A person choosing an insurance plan is also making a financial decision.

Someone managing healthcare expenses may need to consider retirement savings.

A benefits platform capable of understanding both health and wealth can potentially provide much more useful guidance than one focused on only one category.

Nayya's Growth

Nayya's growth accelerated significantly before Liebel became CEO.

According to Forbes, the company generated more than $30 million in revenue in 2025 and reached nearly one million users, with many users accessing Nayya through partnerships with companies such as ADP.

The company has raised approximately $130 million from investors including Felicis, ICONIQ, and Viewpoint. Forbes reported its latest valuation at approximately $515 million, based on PitchBook data, although that valuation dates back to January 2022.

The company has also described a much larger reach when measuring lives served through employer and benefits relationships.

Founder Sina Chehrazi said in late 2025 that Nayya was serving more than four million lives and had grown more than 65% during 2025.

These different metrics—users, paying customers, and lives served—reflect Nayya's B2B2C business model.

Nayya's Enterprise Model

Unlike consumer fintech applications that acquire users individually, Nayya primarily reaches consumers through employers and benefits ecosystems.

This creates a B2B2C model:

Employers → Nayya → Employees

The employer provides access to the platform while employees receive personalized benefits guidance.

Nayya also works with ecosystem partners such as payroll and HR technology providers.

This model gives the company access to large populations without requiring every individual employee to discover and subscribe to the product independently.

The ADP and Workday Ecosystem

Nayya has developed relationships across the broader HR and enterprise software ecosystem.

The company has worked with organizations including ADP and Workday, giving it access to the infrastructure employers already use to manage employees and benefits.

That ecosystem strategy is important because benefits data is inherently fragmented.

Employees' information may exist across:

• HR systems
• Payroll systems
• Insurance carriers
• Retirement providers
• Healthcare providers
• Financial platforms

Nayya's value increases as it can connect those systems and turn fragmented information into personalized guidance.

Trust and Data Privacy

Nayya's business also faces an important challenge: privacy.

Healthcare and financial information are among the most sensitive categories of personal data.

In 2025, Nayya received significant public attention after a Google employee-benefits implementation raised concerns about data sharing.

Google subsequently changed the implementation so that sharing information with Nayya was optional without affecting benefit eligibility. Nayya's leadership emphasized that most of its partners allow employees to control what information they share.

For Liebel, this issue highlights a central challenge for the company.

Nayya can only become a trusted benefits intelligence layer if employees believe that their personal information is handled responsibly.

Sarah Liebel's Leadership Philosophy

Liebel's leadership philosophy combines growth discipline with mission-driven technology.

Several themes stand out.

Make Complex Decisions Easier

Liebel believes technology should reduce the cognitive burden placed on people.

Healthcare and financial benefits are excellent examples because the underlying systems are extremely complicated while the people using them often have little time or expertise to understand every detail.

AI With Accountability

Liebel does not advocate deploying AI simply because AI is available.

For high-stakes decisions, AI needs stronger safeguards and better reasoning.

Her approach is to combine automation with human-centered design, trustworthy data, and appropriate controls.

Scale With Purpose

Her career at Groupon, 1stDibs, BetterUp, and now Nayya has given her experience scaling businesses at different stages.

At Nayya, she is combining that operational experience with a mission centered on healthcare and financial wellbeing.

Information as Empowerment

A recurring theme in Liebel's career is that better information should give people more control.

The objective is not simply to provide more data.

It is to make information understandable enough that people can confidently act on it.

Sarah Liebel's Career Track Record

Liebel's career includes several significant technology milestones:

Groupon → early executive → helped scale company through IPO.

1stDibs → Chief Revenue Officer → helped lead company toward public markets.

BetterUp → President / Chief Growth Officer → led sales, growth, alliances, and consumer products.

Nayya → President & COO → CEO → leading AI-powered benefits transformation.

This gives Liebel a particularly broad operating background.

She has worked with consumer businesses, enterprise technology, marketplaces, digital health, employee benefits, and fintech.

Why Sarah Liebel Matters

Sarah Liebel is interesting because she sits at the intersection of several major technology trends:

AI

Healthcare

Fintech

Employee benefits

Digital health

Financial wellness

The convergence of these categories could create a new class of software designed not merely to administer benefits but to help people make better decisions about their health and financial lives.

Nayya's strategy is effectively to become an intelligence layer for employee benefits.

Sarah Liebel – Key Facts

Category	Details
Full Name	Sarah Liebel
Current Role	CEO
Company	Nayya
Industry	AI / Benefits / FinTech / Digital Health
Joined Nayya	2024
Previous Nayya Role	President & COO
Became CEO	January 1, 2026
Founder	Sina Chehrazi
Previous Companies	Groupon, 1stDibs, BetterUp
Groupon Experience	Early executive through IPO
1stDibs Role	Chief Revenue Officer
BetterUp Role	President & Chief Growth Officer
Education	Tulane University
MBA	Northwestern Kellogg
2025 Revenue	$30M+
Users	Nearly 1M reported by Forbes
Lives Served	4M+ reported by founder
Funding	~$130M reported by Forbes
Latest Reported Valuation	~$515M
2025 Acquisition	Northstar
Core Technology	AI-powered benefits intelligence
2026 Recognition	Forbes Fintech 50

The latest leadership and business figures are based primarily on Nayya, Forbes, The Conference Board, and company statements.

The Future of Sarah Liebel and Nayya

Liebel takes over Nayya at an important moment.

The company has already demonstrated significant growth, raised substantial capital, expanded its user base, and moved beyond healthcare benefits through the acquisition of Northstar.

The next challenge is much larger.

Nayya must prove that AI can become a trusted decision-making layer for some of the most complicated choices people make.

If successful, the company's platform could evolve from benefits enrollment software into an AI-powered personal health and financial guidance system embedded within the workplace.

That would mean helping employees not only choose benefits once a year, but continuously understand how their healthcare and financial decisions affect their lives.

Sarah Liebel's CEO Legacy

Sarah Liebel's emerging CEO legacy is likely to be defined by the idea that AI should make complex, high-stakes decisions easier for ordinary people—not simply automate enterprise workflows.

Her career has prepared her unusually well for that challenge.

She has experience scaling companies through IPOs, building revenue organizations, operating enterprise technology businesses, and working at the intersection of employee wellbeing and digital platforms.

At Nayya, those experiences converge.

The company is attempting to transform benefits from a confusing collection of insurance plans, financial products, and administrative processes into a personalized intelligence layer.

If Nayya succeeds, Sarah Liebel could become one of the executives helping define the next generation of AI-powered healthcare and financial benefits.

For CEO-Watch, her story is particularly compelling because she represents a different kind of modern technology CEO: a seasoned operator taking an AI-native company into a market where better technology could directly improve people's health, financial security, and quality of life.