Vice President Enterprise Sales (Midwest) (Chicago)

About the job

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.

Location: We're looking for someone based out of a major city in the Midwest with an established network in region.

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 close
• 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 close
• Be 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)

Compensation

• OTE range, dependent on location: $250,000-$350,000
• Base range, dependent on location: $125,000-$175,000
• Plus Competitive equity and benefits at a hyper-growth company

Why Join Us

• Join a profitable, mission-driven company at a clear inflection point
• Help shape the GTM engine for a massive, underserved category
• Work with a humble, high-performing team driven by meaningful impact
• Competitive compensation, meaningful equity, and free Goodpath programs for you and your family

Featured benefits

Medical insurance, Vision insurance, Dental insurance, 401(k), Paid maternity leave

Requirements added by the job poster

• 7+ years of work experience with Sales