Head of Sales at MainStreet (Remote)

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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

Our Sales team is the face of our brand, the engine of our rapid growth, and an essential part of the MainStreet product experience. You’ll be directly responsible for driving net-new revenue, with three key dimensions to the role:

People: Hire, develop, and inspire your team while helping to build a strong culture across the Revenue organization.

Process: Drive innovation in our sales process, helping to develop a repeatable, predictable path to scale our team and exceed our goals. Be an expert in our product and help to optimize cross-functional handoffs throughout the customer journey.

Performance: Empower your team to exceed goals through pipeline management, accountability, insightful reporting, and effective planning. 

This is an opportunity to join a growing team at a critical inflection point. Over the next several months we will evolve the business in material ways and we are looking for a Sales Lead to expand our customer base and to ensure that sales quotas are not only met, but exceeded! To be successful in this role, you should have previous experience managing sales operations, while taking accountability for reaching targets. You should also be able to remotely supervise a team of salespeople and set profitable goals. Our ideal candidate will combine excellent communication skills with a strategic mind-set. Ultimately, you will ensure your area of responsibility meets and exceeds the expectations of our business objectives and contributes to our company's success in the long run!

What You’ll Do

  • Create a distinct sales process for reps to follow
  • Establish clear sales objectives for the week, month, year, etc
  • Celebrate sales achievements and goals when met or surpassed
  • Continually monitor and track sales performance, analyze, forecast, and report on monthly sales outcomes in our Monthly Business Reviews, board meetings, and leadership meetings
  • Drive insights that inform our Go to Market strategy and Product Roadmap
  • Collaborate and coordinate with the Marketing, Operations & Product teams in order to maximize customer credits and ensure customer satisfaction
  • Foster a culture of training and coaching in order to ramp new reps and continue building their sales acumen and MainStreet product knowledge
  • Hold frequent performance reviews with your team to provide constructive feedback

What We’re Looking For

  • 5+ years of experience in a sales and direct management experience; directly overseeing a team of Account Executives (minimally 5 direct reports)
  • Proven track record and history of success as an individual contributor within a B2B SaaS sales organization
  • You thrive amidst change and ambiguity, and enjoy working in a fast-paced, high-volume environment, startup company experience preferred
  • You drive immediate impact while laying the groundwork for long-term scale
  • Strong experience working with sales tools (SFDC)
  • Foundational knowledge of SaaS and subscription-based business sales models strongly preferred

You'll Thrive If

  • You enjoy building things from zero to one
  • You’re excited to roll up your sleeves and work on some of the toughest challenges MainStreet has to offer
  • You operate under a service mindset — we’re here to serve our customers, not our egos
  • You enjoy turning complex problems into elegant solutions


  • Base salary for this position is $143,000 - $210,000 and is based upon years of experience that is commensurate with the level of the position, in addition to location
  • Significant Variable Compensation based on team performance
  • 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.

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Candidate Location Eligibility:
Albuquerque, NM
Ann Arbor, MI
Atlanta, GA
Austin, TX
Baltimore, MD
Baton Rouge, LA
Birmingham, AL
Boise, ID
Boston, MA
Buffalo, NY
Charleston, SC
Charlotte, NC
Chicago, IL
Cincinnati, OH
Cleveland, OH
Colorado, CO
Columbus, OH
Dallas-Fort Worth, TX
Dayton, OH
Des Moines, IA
Detroit, MI
Fayetteville-Springdale-Rogers, AR
Greensboro, NC
Hampton Roads, VA
Hartford, CT
Houston, TX
Huntsville, AL
Indianapolis, IN
Jacksonville, FL
Kansas City, MO
Las Vegas, NV
Lexington, KY
Lincoln, NE
Little Rock, AR
Los Angeles, CA
Louisville, KY
Madison, WI
Memphis, TN
Miami, FL
Milwaukee, WI
Minneapolis–Saint Paul, MN
Nashville, TN
New Orleans, LA
New York City, NY
Ogden, UT
Oklahoma City, OK
Omaha, NE
Orlando, FL
Other US Location
Palm Bay-Melbourne-Titusville
Pensacola, FL
Peoria, IL
Philadelphia, PA
Phoenix – Mesa – Scottsdale, AZ
Pittsburgh, PA
Portland, ME
Portland, OR
Providence, RI
Provo, UT
Raleigh-Durham, NC
Reno, NV
Richmond, VA
Rochester, NY
Sacramento, CA
Salt Lake City, UT
San Antonio, TX
San Diego, CA
San Francisco, CA
San Luis Obispo, CA
Santa Cruz, CA
Seattle, WA
Spokane, WA
St. Louis, MO
Tallahassee, FL
Tampa Bay, FL
Tucson, AZ
Tulsa, OK
Washington DC
Wichita, KS
Wilmington, NC

Technology we use

  • Engineering
  • Sales & Marketing
    • JavaLanguages
    • TypeScriptLanguages
    • Node.jsFrameworks
    • SalesforceCRM

An Insider's view of MainStreet

What's something quirky about your company?

Joining a fully remote company, I didn't think it would be possible to form the relationships that I have so far. Its almost weird to me how naturally the employees of MainStreet truly make it a "backyard BBQ" kind of company.


Core Operations Associate, Procurement

How do you collaborate with other teams in the company?

I am always amazed by the talent across the organization. As a Product Manager, I am able to work cross-functionally and experience working with an array of talented people. Not to mention, they are kind people who are genuinely full of joy, positive energy and sometimes quite humorous.


Product Manager

What makes someone successful on your team?

In the first few months I joined MainStreet, I was able to see the dedication and excitement of the team payoff. We were able to standup the Procurement product line and get that up and running. It wasn't just the individual success, but the success of a whole team that was able to accomplish this.


Senior Operations Manager

What is your vision for the company?

Having recently joined MainStreet, I joined because I was excited about the work MainStreet is doing. As a FinTech company helping small businesses, I know that I will be a part of disrupting the market and helping so many businesses along the way.


Head of Quality Assurance

How would you describe the company’s work-life balance?

I spent the last 6-years working living the agency life, which meant hardly any work-life balance. MainStreet helps me protect my energy and creativity, so I can show up as my best self every day.


Senior Brand Designer

What are MainStreet Perks + Benefits

Volunteer in local community
Every employee can take up to 2 days of PTO every year to dedicate to volunteering or political activities, and two hours to vote in any local, state, or federal election.
Partners with Nonprofits
Friends outside of work
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Documented equal pay policy
Unconscious bias training
Diversity manifesto
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Wellness Programs
Retirement & Stock Options Benefits
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Perks & Discounts
Company Outings
Professional Development Benefits
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within

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