Vice President of Engineering

San Jose, CA /
Engineering /
Full Time
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. Then, we introduced MainStreet Procurement, simplifying expense management and contract negotiation for teams without the means to do it themselves, as well as our treasury management product that helps customers earn better yields on their cash reserves.  Since our sort-of viral beginnings in 2019, we’ve raised a $60M Series A (more on that later), launched three product lines (with more in the works), and grew from 3 employees to 160+.

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 100% remote, spanning across 30+ states and Canada. 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 for a Vice President (VP) of Engineering with deep experience leading and growing software organizations of at least 30 engineers. Our VP of Engineering will be responsible for process, talent and effectiveness across the engineering org to deliver with the right balance of consistency, quality and agility to meet business objectives. You’ll be managing engineering managers and ICs across software engineering, SRE, data science, technical program management, and business applications.  You’ll work closely with our product team, to guide execution of the company’s product vision in conjunction with a robust technical roadmap and quality standards.

What you’ll do

    • Track key performance metrics and report on the health and efficiency of the engineering org to senior leadership stakeholders
    • Recruit and retain top engineers and engineering managers
    • Mentor and develop the leadership potential of our engineering managers and senior engineering managers
    • Set and maintain standards and procedures around engineering quality
    • Understand and collaborate on the complete product lifecycle from concept to execution
    • Nurture a supportive and inclusive culture within MainStreet’s engineering organization
    • Collaborate with your peers in product and design to refine the product development lifecycle at MainStreet
    • Iterate on MainStreet’s career ladder for engineers and ensure the team has clear expectations and growth paths

What we’re looking for

    • B.S. and an advanced degree in a technical field required (Computer Science, Computer Engineering, etc.)
    • 10+ years of experience in software engineering
    • 5+ years of experience in engineering management, including managing managers
    • Experience leading and growing engineering organizations of 30+ people
    • Previous experience at a startup and implementing new process from scratch preferred 
    • Strong verbal, visual, and written communication skills with the ability to explain approach to all levels in the organization, including key stakeholders
    • Experience managing and motivating a distributed team
    • Expertise leading engineering in SaaS environments
    • Proven success working closely with Product Management and Design, contributing to the product strategy and helping to successfully deliver on the product roadmap
    • Experience setting technical vision and strategy and developing a robust technical roadmap for an entire engineering organization


    • Base salary range for this position is $230,000 - $275,000 and is based upon years of experience that is commensurate with the level of the position
    • Bonus that is commensurate with the level of the position
    • Robust equity program with significant upside potential
    • Benefits including medical, dental, vision, disability, life, 401k plus additional perks to make your work from home life better
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.