[Hiring] VP, Sales @FSI Services

Role Description

FSI is seeking an experienced and driven VP of Sales to lead our sales organization through its next phase of growth. This is a dual-mandate role: you'll set the strategic direction for how we grow revenue and market share in healthcare, while staying hands-on enough to coach reps in the trenches, work key deals alongside Account Executives, and hold the team accountable to the highest standards of sales execution. You'll own the number — and everything it takes to hit it.

Your Responsibilities

• Team Leadership & Development
  • Recruit, develop, and retain a high-performing team of Account Executives, setting a clear standard for execution, accountability, and professional growth.
  • Run structured coaching programs — including call reviews, pipeline coaching sessions, and deal strategy workshops — to continuously elevate the team's skills.
  • Build a culture of performance grounded in process, data, and continuous improvement.
  • Serve as a player-coach: get in the weeds with AEs on complex deals while maintaining the strategic view needed to lead the organization.
• Revenue Attainment & Forecasting
  • Own the team's quota and drive consistent attainment through rigorous pipeline management and accountability.
  • Maintain an accurate, data-driven forecast — weekly, monthly, and quarterly — and present deal progression and pipeline health to executive leadership with confidence and precision.
  • Identify patterns and gaps in the pipeline early and proactively course-correct with the team.
• Sales Process & Best Practices
  • Enforce and model sales best practices across the team, including MEDDICC qualification, influence and power mapping, and mutual action plans.
  • Ensure AEs are engaging the right stakeholders at the right levels and building the internal champions needed to win complex healthcare enterprise deals.
  • Continuously evaluate and improve the FSI sales playbook based on what's working in the field.
• Industry Strategy & Market Development
  • Develop and execute a go-to-market strategy tailored to the healthcare industry, including health systems, IDNs, and large hospital networks.
  • Serve as an executive presence with key customers and strategic prospects — participate in and lead high-stakes meetings, executive briefings, and deal-closing conversations.
  • Stay current on healthcare industry trends, competitive dynamics, and regulatory shifts that affect FSI's positioning and opportunity.
• Cross-Functional Partnership
  • Partner closely with Marketing, Customer Success, and Product to align on pipeline strategy, messaging, and the full customer journey.
  • Provide structured feedback from the field to inform product roadmap and positioning decisions.
  • Collaborate with executive leadership on headcount planning, territory design, and annual quota-setting.

Qualifications

• 7+ years of B2B SaaS sales experience, with at least 3 years in a people management or sales leadership role.
• Proven track record of building and leading teams that consistently hit or exceed quota.
• Healthcare industry experience strongly preferred — familiarity with health system buying processes, facilities or operations personas, and complex enterprise sales cycles is a significant advantage.
• Deep proficiency with structured sales methodologies — MEDDICC experience required; comfort with influence/power mapping and mutual action plans expected.
• Strong forecasting discipline and the analytical skills to manage pipeline rigorously and present accurately to senior leadership.
• The instinct and willingness to work alongside Account Executives on key accounts and prospects — this role requires both strategic leadership and hands-on deal involvement.
• Exceptional communication and executive presence, with the ability to build credibility with C-suite stakeholders inside and outside the company.
• Experience operating in a high-growth, fast-paced environment where priorities shift and resourcefulness matters.

Work Location

This is a remote-first role. Travel to key customer sites, prospect meetings, and internal team events is expected — estimated at 30–40%.

Compensation

The compensation offered for this position will be based upon relevant experience, qualifications, and work location. The OTE is expected to fall within the range of $250,000 - $325,000.

Our Values

• Customer inspired.
• Solutions-first.
• One team.
• Impactful experts.

We look forward to hearing from you! Don’t meet all the requirements? We’re all on a journey to learn constantly and have areas to develop. If you bring some of the above skills to the table and are still developing in others - APPLY ANYWAY! Learning and experience isn’t a one-way path, if you believe you have the background needed to make an impact in this role, we’d love to hear from you.

FSI is an Equal Opportunity Employer

We are committed to fostering a diverse, inclusive environment and to encourage these values in everyone on our team. We provide an environment of mutual respect where opportunities are available without regard to race, color, religion, sex, pregnancy (including childbirth, lactation, and related medical conditions), national origin, age, physical and mental disability, marital status, sexual orientation, gender identity, gender expression, genetic information (including characteristics and testing), military and veteran status, and any other characteristic protected by applicable law. We believe that diversity and inclusion for people from all walks of life are key to our success as a company.