An employee benefits card for modern companies

Employee Experience Lead at Benepass

Job Type
3+ years
Connect directly with founders of the best YC-funded startups.
Apply to role ›
Jaclyn Chen
Jaclyn Chen

About the role


Benepass helps companies take care of their people. With a single benefits card & mobile app, employees use Benepass to get tax savings on essential expenses like healthcare and childcare, invest in mental & physical health, furnish their home office, join coworkers for Zoom happy hours, take educational courses, and much more! With Benepass, corporate benefits are flexible, cost effective, and easy to use.

Since we graduated from Y Combinator's W20 class, we now cover several thousand employees with Benepass and are growing quickly. Our investors include Gradient Ventures, Y Combinator, and awesome angels like Aaron Levie of Box.

We're a small team looking self-starters and doers. Our professional backgrounds are incredibly diverse ranging from Wall Street to Google/Facebook to barbershops and professional sports. No matter your background, what we care about is passion, attitude, and learning agility.

Employee Experience Lead

As the first experienced hire in Benepass’s Employee Experience (EEX) function reporting to our Head of Strategy and Operations, the Employee Experience Lead will play a critical role in defining and building EEX at Benepass.

The EEX team is the front line team working with both people operations teams and those teams’ employees (Benepass’s end users).

The first class Success function you will help to build is essential to Benepass’s continued rapid growth. You will collaborate closely with our CEO, cofounders, sales leadership, and product as you lay the foundation for one of Benepass’s most important functions.

Your core areas of initial responsibility will be professionalizing both our customer onboarding process, and our account management and renewals processes. The ideal Customer Success Lead will bring a relentless focus on our customers, entrepreneurial leadership in a challenging and highly ambiguous startup environment, and the ability to build systems and processes to help scale the function.

Skills & Experience

We consider candidates holistically; the qualifications below are not hard and fast rules. If you’re interested in the role, apply!

  • 2-4+ years in customer experience organizations with a record of achievement and increasing responsibility
  • Deeply empathetic; strong POV on the right tone and approach to work with diverse stakeholders, and the ability to and develop this in others
  • Demonstrated ability to create a high performing culture; record of growth and development for the individuals and teams you’ve managed.
  • Deep familiarity with CX tools, systems, and processes. Strong POV on systems and processes to build effective organizations, and the tooling needed to support these systems.
  • Prior startup experience a plus. Thrives in ambiguous environments.
  • Bonus points for experience working with HR / people operations teams.

What we offer

  • Competitive compensation for a seed stage startup
  • 95% coverage of medical, dental, and vision
  • Benepass benefits, including $500 WFH setup, $150/month cell phone + internet, $100/month Wellness
  • Work wherever you want (though we ask you to work in a US time zone)
  • Flexible PTO
  • Startup magic with a highly collaborative, effective group that's obsessed with serving our customers

Why you should join Benepass

Benepass (YC W20) helps companies take care of their people; employees get a single card for all of their benefits, paired with a friendly and intuitive mobile app. Our product makes it easy for employees to save on essentials (like child- and healthcare) and to enjoy their company’s perks (think work from home setups, fitness memberships, and free lunch) especially in a remote-first world. We also automate away tons of manual work that companies usually have to do to manage benefits.

Our investors include Gradient Ventures, Y Combinator, and awesome angels like Aaron Levie of Box.


Benepass is using modern software, automation, and a great UX to transform the $30+ billion benefits industry. We’re displacing incumbents running on manual processes and legacy technology, like fax, checks in the mail, and artisanal CSVs.

To do that at scale, we need to solve hard technical problems involving payments, security, integrations, NLP, nightmarishly complex and ever changing rules, automation, and a whole lot more. We also have to deliver an incredible user experience through our web and mobile apps.

We know we’re on to something here: In the past year, we’ve grown to cover thousands of lives and signed big customers who are household names. We've found product-market fit and we’re growing at breakneck speed.


In my opinion, one of the biggest reasons to work here is the team you’ll be joining. I love that I get to work with a team who are not only smart and super capable, but are also really friendly and genuinely care about each other.

Background-wise, we run the gamut, from Wall Street to Google & Facebook to barbershops and professional sports.

(Also, nerd sniping each other is the company sport. Frequent topics include robotics, AI, synthetic biology, dev tools, rockets, WSB, cryptography, and our pets.)