Head of Sales


You’re a rock star B2B sales professional – a boots on the ground closer who also enjoys building and managing a team. You’re a creative prospector, have a bias for action, and are scrappy in your execution.  Beyond that, you’re a model of integrity and are completely customer obsessed.  

Just like us.


We’re GroundCloud. A high growth $50M start-up launched in 2017. With your help, we’re poised to skyrocket to $1B.

Our better-than-sliced-bread service? We’ve solved some pretty big efficiency, compliance and safety problems for final-mile logistics contractors and their delivery fleets. Currently that includes about 60% of the 5600 contracted companies providing ground service to FedEx.

Our one-of-a-kind flagship platform has become the gold standard in delivering fully integrated operations, boosting our customers ROI by lowering their operating and insurance costs. Listen to this testimonial from a raving fan!

Now we’re ready to break the sound barrier by exploding our market share in the final mile space.

We’re just waiting for you to help us close the deals.


Since we’re at an inflection point in our growth, we’ll need you to build out our sales infrastructure. Starting with two inside sales reps, you’ll grow the team to include external reps who will help you source and convert leads in target markets. You’ll partner with our COO, VP of Marketing, Product and other internal teams to build and execute on a sweeping sales strategy to meet the company’s growth goals; recruit and lead a team of sales professionals; and oversee revenue growth goals.

Here are the specifics:

  • Create and communicate a sales strategy aligned with our business goals and objectives.
  • Build, train, and mentor a sales team with a hands-on, player-coach approach.
  • Partner with the VP of Marketing to create and execute go-to-market strategy, and create strong lead generation, follow-up, and conversion.
  • Develop sales plans and strategies with measurable success metrics and an annual sales budget. Motivate the team to meet and exceed sales goals.
  • Ensure alignment with the executive leadership team to include Customer Support, Inside Sales, and Product.
  • Develop a highly effective personal presentation of all GroundCloud’s products and services.
  • Communicate evolving needs of customers and/or market to include content, service enhancements, and competitive developments.


  • You have 10+ years of conceiving and executing successful B2B sales efforts to meet sales targets.
  • You have proven experience in sales of SaaS solutions to both SMBs/entrepreneurs and Midmarket/Enterprise accounts.
  • Ideally, you’ll have established relationships with potential customers and channel partners in the Transportation and Logistics verticals.
  • You have outstanding consultative selling abilities and excellent interpersonal skills with executive level customers and partners.
  • You have prior success in building and leading a sales team, specifically outbound sales reps.
  • You have experience using Salesforce, HubSpot and/or Pardot, or equivalent.
  • You thrive in a fast-paced, high-performance environment
  • You’re collaborative, inspirational, and an expert influencer
  • You can navigate difficult conversations with a refined touch
  • You’re a seasoned team leader able to pivot between strategy, brainstorming, and hands-on execution
  • You take initiative, lead by example, and achieve consistent results
  • You’re comfortable working with a distributed team across functions and geographies
  • You’re humble about your superpowers and can lighten the load with levity!
  • You’re a role model for our company culture – hard work, honesty, integrity, continuous improvement, and innovation.

LOCATION: Fully remote but feel free to work from our Minneapolis office if you’re local.

COMPENSATION: $150,000 + incentive compensation

Benefits include:

  • 401(k) with 10% company match
  • Dental insurance
  • HSA account with company match
  • Health insurance
  • Paid time off
  • Vision insurance


This is a retained search, so we ask that you work directly with our recruiter, Shira Lotzar of Purposeful Hire. Please send your resume and cover letter to: shira@purposefulhire.com.

We expect a lot of competition for this role, so make it abundantly clear why YOU’RE the rock star we’ve been seeking!