Director of Core Operations

Remote Position /
Operations /
The problem

Every year, billions of dollars are set aside by your local, state, and federal representatives to make it easier for anybody to build a small business and turn their dream into reality.

But while governments might be great at governing, they’re terrible at marketing. These billions sit unclaimed, waiting for founders to discover them. We want to fix that, and we need your help.

The opportunity 

MainStreet is looking to add a Director of Core Operations to help us build and scale our core business, and own strategic initiatives across the organization. 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. You’ll report directly to our VP of Operations, Lena Gratz.

What you'll do

    • Own and run the day-to-day operations behind one of MainStreet’s core product offerings
    • Build and manage a team of strong operations managers to expand your impact and reach
    • Coach your team to run the business efficiently and effectively, and empower them to implement processes and procedures that support MainStreet’s hyper-growth
    • Work with cross-functional exec team to define and execute projects of strategic importance across the organization
    • Scope and lead nascent initiatives that will contribute to MainStreet’s growth goals

What we're looking for

    • 8+ years of relevant experience in Operations, Program management or similar
    • 5+ years of team management experience
    • Ability to bootstrap nascent initiatives & own complex projects end-to-end
    • Ability to juggle competing priorities in high growth environment
    • Champion problem solver without hesitancy to roll up their sleeves
    • History of building scalable processes, and translating strategic plans into action
    • Familiarity with the unique challenges of SMBs in the tax, FinTech, Procurement and/or SaaS environment and passion to build effective SMB solutions
    • Understanding of FinTech and industry trends, comfortability with rolling out new financial products and offerings
    • A willingness to learn on the job and take on tasks as needed
    • Excellent communication skills
    • Ability to work independently and communicate over the phone and with video chat software, such as Zoom


    • Base salary range for this position is based upon years of experience that is commensurate with the level of the position in addition to location
    • 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
    • Flexible PTO
About MainStreet

What we do

We make these tax credits easy as butter. MainStreet pairs companies & employees with hundreds of local, state, and federal tax programs. Then we do all the paperwork to get companies what they’re owed in minutes, vs the dozens of hours it would otherwise take.

The average company gets $51,040… in the first year. In cash. 

We just announced our $60M Series A, led by SignalFire. We’re backed by an incredible community of partners, operators, and founders, including Ryan Hoover (Product Hunt founder), Ashton Kutcher’s Sound Ventures, Des Traynor (Intercom cofounder), Gradient (a Google Venture Fund), Ron Conway’s fund SV Angel, 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.