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Mid-Market Account Executive



Sales & Business Development
Remote · United States
Posted on Tuesday, July 11, 2023
Who is Aiwyn and what do we do?
Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 80+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by a Top 10 fintech VC.
Who are you?
As a Mid-Market Account Executive at Aiwyn, you’re responsible for selling Aiwyn software and services to prospective customers (top-ranked CPA firms), and cross-selling new solutions to current customers.

What You Will Do: Hit a ~7 figure annual sales quota by...

  • Master a Challenger-based, MEDDPICC-qualified sales process
  • Source and qualify new leads (outbound, website, in-person events)
  • Lead Discovery and Demo meetings
  • Create and present tailored business cases to C-level decision-makers
  • Negotiate multi-year SaaS contracts with multiple stakeholders
  • Collaborate with Aiwyn’s Customer Success team to drive cross-sells

You'll thrive in this role if you have experience...

  • Working hard and hitting quota at a post-Series A B2B SaaS company
  • Adapting to change and seeking coaching, always learning
  • Closing $5-6-7-figure $ARR SaaS contracts, ideally with professional services firms
  • Operating with a good humor and a bias for helpful action… selling technology solutions to large professional services firms (CPA, law)
  • Running a Discovery-centric sales process with curiosity
  • Relentlessly and proactively engaging with C-level buyers to drive urgency
  • Using tools (Hubspot, Gong) to get leverage and drive self-accountability, improvement
  • Traveling extensively (up to 50%), getting face to face with firm leaders
  • Managing multiple Champions, Influencers, Economic Buyers in each prospect account

Why Work at Aiwyn? The Big Picture:

  • Great compensation, and you’ll work with A-players to accelerate an already-fast growing business that serves a growing sector of the economy. Other details below..Aiwyn customers love Aiwyn (Net Promoter Score is 82), paving the way for ongoing growth.
  • Because of bullet #1, we’re seeing a flywheel of referrals and prospective customer interest.
  • We’re rolling out 2 new solutions in ‘23, giving our GTM teams more assets to serve the market.
  • Aiwyn is led by serial entrepreneurs with multiple exits and funded by a Top 10 fintech VC.
  • Inside scoop: Accounting is one of the few economic sectors that is growing, even in a difficult economy – what’s more, most firms are actually turning away new business because the profession is facing a talent shortage (fewer CPAs are entering the market). Aiwyn’s solutions help solve this profession-wide talent shortage issue by automating tasks and unlocking time and capacity so that firms can take on more work and realize greater profits from that work. LSS, we’re helping firms pick up the money that’s on the ground…
  • If you’re making a long-term bet on where to continue your sales career, this is a smart one.
  • Base + uncapped commission plan
  • Stock options
  • Healthcare benefits
  • 401(k) matching
Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations, and ordinances.
Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: