At Winnie, we’re on a mission to make parents’ lives easier. Winnie helps over 7M parents across the United States find daycare, preschool, and more. In addition to helping parents, child care providers use Winnie to fill their open spaces, build their wait lists, and get support and resources to run their business efficiently.

As a Sales Representative, you’ll help child care businesses understand the value of Winnie and drive leads and enrollments through our platform.

About the Role

We are looking for a Sales Representative to grow our outbound and inbound sales development efforts to childcare businesses. This is a great opportunity for an entrepreneurial Sales Representative who wants to grow their career quickly through full-cycle sales backed by a world-class product team. This role reports directly to the CEO and co-founder and offers considerable support from the Product team and Senior Leadership.

The primary responsibility of the Sales Representative is to target childcare enterprises with $20M-200M annual revenue who will use Winnie’s digital marketing services to reach more families. The target market accounts for more than $30B in annual revenue and includes national and regional childcare companies, including multi-location companies, franchise businesses, and nonprofits looking to grow enrollments and waitlists. This is a high-energy, client-facing sales role requiring proven sales ability with a passion for closing deals and growing strategic accounts.

This position is remote-friendly and we are open to candidates based anywhere in the U.S. Currently, during the COVID-19 pandemic, our team is distributed across the U.S. and we are hiring and onboarding new teammates virtually.


  • Research accounts in depth, identify key targets and generate interest
  • Execute outbound phone and email campaigns to book discovery calls
  • Conduct discovery calls with senior level executives and stakeholders serving as the first touch-point for prospects
  • Clearly articulate the Winnie value proposition to different segments of the SME childcare market
  • Work closely with CEO to close deals
  • Establish a collaborative business relationship between Winnie and childcare businesses to nurture and grow strategic accounts
  • Provide actionable product feedback to the Product Team to help iterate on our value offering to childcare businesses


  • 5+ years of sales experience
  • Demonstrated B2B sales experience consistently exceeding quota
  • Quick learner and self-starter comfortable working remotely and independently to achieve goals
  • Excellent verbal and written communication skills
  • Ability to translate technology and data to a non-technical audience
  • Proficient in GSuite, a Sales CRM (we use Hubspot), and other remote tools
  • Experience working for a technology startup or SaaS company preferred

What it’s like working for Winnie

  • We’re not your typical tech company
  • We are super family-friendly and value reasonable work hours
  • We are committed to a diverse and inclusive work environment, and we are supportive of returners who have been out of the workforce
  • We work cross functionally and collaboratively across the company
  • We use Slack and video calls to facilitate communication with remote employees

What we offer

  • Generous equity package and a competitive salary and commission
  • Excellent medical, vision, and dental coverage for employees and their families
  • FSA option, 401k plan, commuter benefits
  • Generous vacation policy (and we use it)
  • 12 weeks of fully paid parental leave and family friendly policies
  • Professional development budget for each employee

We are an equal opportunity employer and value diversity at our company. Don’t meet all the requirements for the position? That’s okay. We encourage you to still apply.