Ready to Develop High-Performing Sales Teams in Complex Selling Environments?

We're looking for an experienced Enterprise Sales Leader who thrives on developing teams and driving results in the dynamic world of HR, Benefits, and Talent Management. As our Regional Vice President you'll combine strategic thinking with hands-on support to help your team achieve ambitious revenue targets.

What makes this role different

✓ Team development focus: Coach and develop mid-career and senior enterprise sales directors in fast-paced, complex environment

✓ Strategic territory management: Develop comprehensive plans to maximize revenue from assigned market segments and accounts

✓ Collaborative leadership: Work closely with broader sales management team to ensure alignment with corporate initiatives

✓ Cross-functional impact: Partner with implementation, client success, and marketing teams to deliver seamless client experience

Achieve revenue excellence: Meet and exceed Annual Recurring Revenue targets in specific geographic and market segments while maintaining strategic focus.

Develop your team: Coach and develop team members to improve key productivity measurements while fostering culture that balances performance, productivity, and engagement.

Lead strategic planning: Develop territory plans that maximize revenue opportunities while leveraging Salesforce.com for accurate forecasting and reporting.

Support sales activities: Work directly with team members to demonstrate solutions via presentations and support proposal delivery to prospective clients.

Ensure seamless transitions: Coordinate with Implementation Services and Client Success on pre/post-sales processes and client hand-off procedures.

Drive demand generation: Collaborate with Marketing to support voice of customer initiatives and influence demand generation efforts and mindshare creation.

What You Bring to Our Mission

The leadership foundation:

• Bachelor's degree or equivalent experience
• 5-10 years of sales management experience in Wellbeing, Benefits, or HR technology category
• Documented history of consistent team quota over-achievement
• Understanding of culture and desire to be part of high-performing team

The sales expertise:

• Experience selling and directing enterprise products/services with value-based selling methodologies
• Proficiency in managing lengthy complex selling engagements (6-9 month sales cycles)
• Strong familiarity with sales productivity tools (Salesforce.com, SalesLoft, Sales Navigator, Zoom)

The professional qualities:

• Strategic sales capabilities with comfort communicating at all organizational levels
• Self-directed and results-oriented with strong project management and influencing skills
• Excellent understanding of B2B prospecting and sales best practices with creative problem-solving abilities

This is a remote role with a strong preference for candidates based in one of these locations: Chicago, Boston, New York, Philadelphia, Charlotte, or Atlanta. Role requires up to 50% travel.

Benefits

The Highlights:

• Competitive base salary and benefits effective day one
• Comprehensive medical and dental through our own health solutions (yes, we use what we build)
• Unlimited PTO—rest and recharge time is non-negotiable
• Mental health support, retirement planning, and financial protection
• Professional development with clear career progression and learning budgets
• Mission-driven culture where diverse perspectives drive real impact on people's health

Want the full picture? Visit personifyhealthbenefits.com to explore our complete benefits package, wellness programs, and other employee perks.

Compensation: This position offers a base salary range of $161,000 - $244,000, depending on location, skills, and experience. You're eligible for our full benefits package starting day one.