Demo

Risk Solutions Sales Leader | Player | Coach

Questpro
Orlando, FL Full Time
POSTED ON 1/2/2026
AVAILABLE BEFORE 2/7/2026
  • Location: Orlando, FL
  • Remote: Remote
  • Type: Questpro - Contingent
  • Job #21438

Risk Solutions Sales Leader | Player | Coach

Location: East Coast, Florida preferred — remote-flexible within region

Why This Role Is Exciting

Step into a high-impact leadership role where you not only manage and coach a team of top-performing sales professionals but also personally drive net-new revenue. Perfect for entrepreneurial sales leaders who thrive on growth, autonomy, and co-creating strategy with C-suite executives.

About The Company

QuestPro is assisting a fast-growing risk and COI management solutions provider at the forefront of modernizing compliance and risk processes for enterprise and mid-market organizations. This is a chance to shape sales strategy and help drive company-wide growth initiatives.

Who You'll Be Calling On

Target Verticals: Construction, Real Estate / Property Management, Insurance Carriers, TPAs, Self-Insured Employers, Risk & Compliance Service Providers

Buyer Titles

  • Risk Manager / Director / VP
  • Compliance Officer / Director / VP
  • Legal Counsel / General Counsel
  • Procurement / Vendor Management / Operations Leaders
  • Safety / HSE Leadership
  • Insurance / TPA Account Managers

What You’ll Do

  • Lead, mentor, and develop a team of growth-oriented sales professionals while maintaining your own quota.
  • Drive net-new business in enterprise and mid-market accounts.
  • Develop and execute territory and team strategies to maximize pipeline and revenue.
  • Partner with marketing and product teams to execute targeted campaigns and solution adoption.
  • Coach your team on entrepreneurial sales techniques, consultative selling, pipeline management, and closing strategies.
  • Collaborate closely with C-suite executives to co-create company and sales strategy.
  • Track and report on team and personal sales performance and forecast accuracy.
  • Represent the organization at industry events, webinars, and client meetings as a thought leader.

Who You Are

  • Proven top-performing individual contributor in B2B SaaS or insurance/risk technology sales.
  • Experienced in leading and coaching high-performing teams.
  • Comfortable in fast-growing, entrepreneurial, startup-style environments.
  • Deep understanding of risk management, compliance, and COI processes.
  • Skilled at engaging C-level and senior stakeholders.
  • Self-motivated, results-driven, and enjoys balancing leadership with personal sales responsibilities.
  • Resides on or near the East Coast (Florida preferred), willing to travel as needed.

Why You’ll Love Working Here

  • Competitive base uncapped commission / bonus plan.
  • Leadership role with entrepreneurial impact — shape culture, process, and strategy.
  • Opportunity to personally contribute to revenue while scaling a high-performing team.
  • Flexible work environment with remote options.
  • Career progression into executive sales leadership or regional management roles.

Related Role: BDR, Account Executive same target sales vertical

Contact Recruiter jpomelow@questpro.com

Salary.com Estimation for Risk Solutions Sales Leader | Player | Coach in Orlando, FL
$82,063 to $105,737
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