VP, Software Sales

Accountabilities:

• • Own the direct software sales number, including bookings, pipeline targets, conversion metrics, forecasting, and overall revenue performance.
  • Build, hire, onboard, and ramp SDR and AE teams from the ground up, establishing clear performance expectations, ramp plans, and compensation inputs.
  • Design and continuously refine the end-to-end sales motion, including outbound sequences, qualification frameworks, SDR-to-AE handoffs, pipeline stages, forecasting, and deal management.
  • Personally develop and test outbound messaging and sequences during the early stages of the sales motion before establishing repeatable team processes.
  • Lead customer-facing product demonstrations, executive presentations, and strategic sales conversations while setting a high standard for the broader sales team.
  • Establish the pipeline mathematics and operating cadence required to create predictable performance, including weekly forecasts, pipeline reviews, and deal inspections.
  • Partner closely with channel and partner teams to ensure the direct sales motion complements and strengthens existing partner-led opportunities.
  • Collaborate with Marketing on account-based marketing, content, demand generation, and programs that create qualified opportunities for the direct funnel.
  • Monitor sales performance and provide clear, data-driven updates on pipeline health, conversion, forecasting, and team productivity to executive leadership.
  • Contribute to pricing and packaging strategy, including discount discipline and deal-level pricing decisions that support sustainable growth.
  • Identify opportunities to improve the sales organization, processes, and customer journey as the business scales.
  • Take on additional strategic initiatives and projects that contribute to the growth and success of the organization.

  Requirements

  • Proven direct SaaS sales leadership experience selling to IT, MSP, cybersecurity, or related technology buyers within mid-market organizations.
  • Previous VP or Director-level sales leadership experience with direct ownership of revenue, quota, sales teams, and pipeline targets.
  • Demonstrated success hiring SDRs and AEs from the ground up and developing them into productive, high-performing teams.
  • Experience managing B2B SaaS sales cycles typically ranging from 60 to 180 days.
  • Strong hands-on understanding of SDR-to-AE sales motions, including outbound sequencing, qualification criteria, call inspection, handoffs, and pipeline management.
  • Demonstrated ability to lead executive-level sales conversations, deliver compelling product demonstrations, and coach sales professionals to a high customer-facing standard.
  • Experience working alongside channel, partner, or co-selling organizations in a multi-channel go-to-market environment.
  • Track record of scaling a direct sales segment, function, or business unit through multiple stages of growth.
  • Experience shaping SaaS pricing and packaging strategies, managing discount discipline, and making sound deal-level pricing decisions.
  • Strong analytical and operational skills, with the ability to understand pipeline performance, identify conversion gaps, and build actionable sales plans.
  • Highly hands-on, entrepreneurial approach with the ability to build processes from scratch rather than simply inherit established systems.
  • Strong communication skills, executive presence, coaching ability, and commercial judgment.
  • Comfortable operating with specificity and accountability, including clearly articulating performance trends, early mistakes, lessons learned, and corrective actions.
  • Ability to thrive in a fast-paced, evolving environment where priorities and sales strategies may change as the business scales.

  Benefits

  • Competitive compensation: Competitive base salary plus commission, with target total earnings of $280,000–$320,000+ OTE.
  • Growth opportunity: Significant opportunity to shape and scale a software sales organization within a high-growth business.
  • Medical coverage: Generous medical insurance for eligible full-time employees.
  • Dental and vision: Comprehensive dental and vision coverage.
  • Flexible time off: Flexible paid time off to support work-life balance.
  • Retirement: 401(k) plan to support long-term financial planning.
  • Remote work: 100% remote position within the United States.
  • Innovation-focused culture: An environment that encourages bold ideas, strategic thinking, and entrepreneurial initiative.
  • Meaningful impact: Direct influence over revenue growth, sales strategy, team development, and the evolution of the software business.
  • Team experiences: Company events and opportunities to connect with colleagues.
  • Employee perks: Friday DoorDash lunches and employee referral bonuses.