is the leading technology solution for busy eCommerce sellers to manage sales tax and is trusted by more than 20,000 businesses.
Our core values
  • We know that we’re better together
  • We are always learning and growing
  • We shape our own destiny
  • We build relationships that matter
The TaxJar team at Stripe is on a mission to help businesses of all sizes take advantage of TaxJar’s market-leading sales tax compliance software. We are looking for a talented and innovative leader to strategically build and lead the TaxJar sales organization, while working closely with both the TaxJar and Stripe teams to develop and execute a strategy to ensure the TaxJar team becomes a thoughtfully integrated and successful part of the Stripe sales model. This is an exciting opportunity to be in the first blended role between TaxJar and Stripe. The Head of Sales will help us to build the future of sales together and this first leg of the journey is just the beginning.  
You will be tasked with building upon the successes of the company’s existing sales organization while  implementing the necessary organizational changes required to build the infrastructure capable of rapid growth. You are an established and respected executive who brings credibility to the company with employees, customers, partners, and vendors. You’ll lead and coach a team of ~35, including, Sales Managers, Account Executives, Account Managers, Sales Development Reps, plus our Sales Operations and Partnership Teams. You will be an integral member of both the TaxJar and Stripe sales leadership teams. In addition, you’ll work closely with TaxJar’s CEO and Stripe’s Global Head of Product Sales to integrate TaxJar into Stripe’s broader go-to-market efforts. You will roll up your sleeves to work directly with prospective TaxJar and Stripe customers. 
We are looking for a self-starter who has demonstrated success dealing with ambiguity, operating in a high-growth environment, and solving complicated problems with limited oversight. Ideal candidates will have experience in managing an organization through change or integration, scaling a technology sales team, superb communication, and a knack for matching strategy to customer needs. Individuals applying for this role must be entrepreneurial and self-driven with a passion for building something new.
You will…
  • Build the long term vision and strategy for the TaxJar Sales team in conjunction with TaxJar and Stripe leadership while managing day-to-day operations
  • Ensure TaxJar and Stripe consistently deliver on revenue and growth targets across various customer segments
  • Recruit, train, and lead a metrics-based, sustainable, winning sales culture for a remote / fully distributed sales, partnership (channel) and account teams, developing a diverse and highly motivated team of individuals to meet or exceed quota
  • Work collaboratively with peers on the Stripe and TaxJar leadership team (including Marketing, Finance, Product and more) to define, iterate on, and execute a cohesive go-to-market strategy
  • Develop and enable long term plan to thoughtfully and purposefully integrate TaxJar’s sales team into Stripe’s global go-to-market organization and ensuring that both teams are well-positioned for combined success in the transition

We’re looking for someone with…
  • 10+ years of leadership and strategy experience, including experience leading technology sales
  • Proven track record of execution and change management skills in a high growth environment, including the ability to build meaningful relationships with reports and peers
  • Ability and passion for hiring, training, and coaching a high-performance sales team
  • Strong communication skills, including ability to clearly communicate technical concepts 

We’ll see it as a bonus if you also bring…
  • Experience leading a team and organization through an integration 

TaxJar is a human-first company
People are accepted and free to be who they are.
We embrace that diversity, equity, inclusion and belonging are essential sources of creativity and innovation that bring a richness of thinking and experience to the work that is celebrated at TaxJar. Simply put, we care. We will always put people – our team and our customers – first, by supporting our people to do their best work building products our customers love. 
Our formula is simple. We believe we have an elevated level of responsibility in everything we do. This means we empower our team to do the right thing for each other and for our customers, and we do the right thing, even when it’s harder. We’ve built a team based on trust, that endeavors to maximize our team members’ individual talents so our workplace creates a sense of meaning and belonging for everyone.
Read our 2020 Diversity, Equity, Inclusion and Belonging report here.
  • Excellent health, vision and dental benefits
  • Generous PTO policy
  • Professional development funds
  • Company retreats (fully paid for by us of course)
  • 12 week paid maternity/paternity leave
We offer all of our full-time employees amazing benefits. Visit www.TaxJar.com/careers for a full list of our benefits and to learn more about how we work and what we stand for.