Work at a Portfolio Company

VP of Customer Experience



Customer Service
San Francisco, CA, USA
Posted on Saturday, July 8, 2023
At MainStreet, we’re problem solvers.
Our products aim to do one thing: save startup founders and small business owners time, money, and peace of mind. We started by demystifying complicated tax credits, saving over $100M – and countless hours of tax code research 🥱– for founders in nearly every industry. Since our sort-of viral beginnings in 2019, we’ve raised a $60M Series A, expanded our product lines (with more in the works), and grew from 3 employees to our current team!
We owe our success to the strength of our team. Before joining MainStreet, we helped build companies like Intuit, PayPal, Google, Apple, Coinbase, Gusto, LinkedIn, Slack, and more. We’re fellow founders, engineers, accountants, designers, dog (and cat) lovers, adventurers, coders, and parents. We move fast. We think big. We don’t take ourselves too seriously. And we’d love for you to join us.
The opportunity
MainStreet is looking to add a VP of Customer Experience to help us scale our Customer Support and Success Teams. You will have the opportunity to actively shape the future of a FinTech company that promises to contribute to the success of startups and SMBs.

What you’ll do

  • Scale and manage both the Customer Success and Customer Support functions (together: CX), servicing our fast growing business on path to >10X customer base
  • Strong understanding of the unique dynamics involved in servicing different customer segments, e.g. acquired via direct vs. partnership sources and its unique challenges, e.g. branding, collaborating with partner support teams, rapid scale…
  • Develop and execute strategies to optimize the customer journey and enhance the experience for different customer segments in times of fast growth
  • Set and monitor KPIs to measure customer satisfaction, retention, and ACV, and implement initiatives to continuously improve these metrics
  • Collaborate closely with XFN teams (e.g. Sales, Product, Ops) to align customer experience initiatives with company objectives
  • Establish and maintain strong relationships with key stakeholders, including executive leadership, to drive customer-centric decision-making and advocate for the voice of the customer
  • Provide leadership and mentorship to the Customer Success and Customer Support teams, fostering a culture of excellence, collaboration, and continuous learning

What we’re looking for

  • 12+ years experience in a leadership role scaling and managing Customer Success and Support teams, ideally in a corporate and/or startup FinTech or SaaS environment
  • Proven track record of successfully driving customer success and satisfaction, with a strong focus on delivering exceptional customer experiences
  • Strong track record of successfully building and managing relationships with external partner, measured by renewals and revenue increases
  • Strong analytical and problem-solving skills, with the ability to leverage data and insights to drive decision-making and optimize customer journeys
  • Experience in developing and implementing scalable processes and systems to enhance operational efficiency and support customer success initiatives
  • Excellent communication and interpersonal skills, with the ability to collaborate effectively with cross-functional teams and influence stakeholders at all levels
  • Ability to inspire and motivate teams to achieve high performance; comfort with autonomy and being a hands on leader
  • Proactive and adaptable mindset, with the ability to thrive in a fast-paced and evolving startup environment
  • Positive energy, optimistic about the future and determined to get there. Passionate for our mission to empower small businesses to create jobs and opportunities


  • Base salary range for this position is $220,000 - $260,000 and is based upon years of experience that is commensurate with the level of the position
  • Robust equity program with significant upside potential
  • Benefits including medical, dental, vision, disability, life, and 401k
About MainStreet
MainStreet takes a holistic approach to small business management so you can grow smarter, not harder. We plug into your accounting and payroll systems to check for savings opportunities in unlikely places. From complex government tax credits to exclusive discounts on the tools you use every day, we save you thousands of dollars, hundreds of hours, and countless headaches.
Throughout the year, you’ll track expenses and savings through your MainStreet dashboard and tag us in on big purchases and contract negotiations. Come tax season, we’ll do the paperwork and even let your CPA take all the credit. Consider us your silent partner-in-savings, your financial secret weapon, your smart (not a) bank – whatever you want to call us. We’ve got your back so you can get back to building your business. ✨
Our $60M Series A
We’ve raised over $60M from an incredible community of partners, operators, and founders, including SignalFire (who led our Series A), Ryan Hoover (Product Hunt founder), Ashton Kutcher’s Sound Ventures, Des Traynor (Intercom co-founder), Gradient Ventures (a Google Venture Fund), Ron Conway’s fund SV Angel, Shrug Capital, and Tusk Ventures.
How we think about diversity
We try to make sure the diversity of our customers is reflected in the team that serves them. Because when we include people of all races, genders, sexual orientations, ages, and identities — we end up building a better experience for everyone who uses MainStreet.
We know we need to be intentional in our hiring practices in order to overcome systemic biases we may be blind to. So, if your lived experience has given you a unique perspective on business, startups, or any other aspect of our business – even if you don’t meet all the requirements – please still apply and let us know so we can make sure your application gets the attention it deserves.