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Vice President Enterprise Sales (Midwest

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Goodpath
Full Time position
Listed on 2026-08-04
Job specializations:
  • Sales
    B2B Sales, Business Development, SaaS Sales
Salary/Wage Range or Industry Benchmark: 120000 - 190000 USD Yearly USD 120000.00 190000.00 YEAR
Job Description & How to Apply Below
Position: Vice President Enterprise Sales (Midwest)

Own deals. Advance our GTM. Help build a category-defining company.

About Goodpath

Goodpath delivers integrative, AI-powered care for chronic conditions - blending 22 medical disciplines into one personalized experience. We partner with employers, payors, and platforms to reach members – delivering industry-leading engagement and outcomes. We doubled ARR last year, are already profitable, and are closing our Series A to scale.

The Role:

We’re hiring an Account Executive to drive new logo sales to benefits leaders at enterprise employers. You’ll lead complex sales cycles, often partnering with benefits consultants. You’ll sell a proven, multi-condition healthtech solution with a consultative, value-oriented approach. As part of our early GTM team, you’ll help shape how sell – building on our track record of beating quota scaling toward $100M+ ARR.

What

You’ll Do
  • Own your number: maintain pipeline, forecast with accuracy, and deliver against annual quota/
  • Run complex, high value deals: sell to leadership at top employers, from qualification to clo
  • se Generate pipeline: partner with our BDR, channel, and marketing teams to generate addressable pipeline
  • Partner with benefits consultants to generate pipeline and co-sell, developing trusted relationships.
  • Lead strategic RFPs: coordinating internal stakeholders and driving process to clo
  • seBe the CEO of your customer and territory. Deeply understand buyers, tailor for value, and manage journey from sale to success.
What you bring to the table
  • 7+ years in B2B sales, including 2+ selling to HR, total rewards or benefits buyers
  • Proven track record: you’ve consistently hit quota, and can articulate what worked – and what didn’t – when you missed
  • Proven ownership of complex sales cycles (6-9+ months) and partner-driven motions
  • Excellent discovery and storytelling skills – you translate pain to clear value
  • Early-stage builder: you thrive in ambiguity and are energized by building
  • Team-first mindset and excellent communicator
You’ll be successful here if you:
  • You know the industry playbook s a nd how to adapt them for each buyer
  • You own your results and keep learning from every win, miss and bet
  • You want to build something great, together: our success is your success and vice versa
  • You’re resourceful when the path isn’t clear (you “draw the owl
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