Lead and scale a mid-market full-cycle sales organization: hire, coach, and manage AEs to hit quota; own pipeline, forecasting, and revenue predictability; serve as executive sponsor on strategic deals; build enablement, onboarding, comp plans, and cross-functional feedback loops to product, engineering, and marketing.
UserGems is the AI Command Center for outbound and ABM. Think of us as the ‘brain’ behind your go-to-market. We capture account & contact data and buying signals to help companies know who to target, when, and why. Then, take the next actions via humans or AI agents to run personalized outbound and ABM at scale.
UserGems has generated billions in pipeline and revenue for hundreds of start-ups and public companies. Companies like Hubspot, Workday, Crowdstrike, Mimecast, UserTesting, SAP, Outreach see more than 15X ROI in closed-won revenue from UserGems.
We’re looking for a hands-on VP of Sales who thrives in high-growth environments. You’ll partner with the CEO and leadership team to refine our sales strategy, strengthen and scale our existing team, and build the operational structure needed to scale from 70 to 100+ employees.
What you’ll own:
Team leadership
- Lead, coach, and scale a team of full-cycle mid-market & enterprise AEs and AMs from individual contributors to frontline managers
- Design and evolve team structure as we scale from $20M to $50M to $100M ARR
- Maintain a high-performance culture with clear expectations and performance management frameworks
- You’ll be a true player-coach - jumping on a call, running a demo, or working a deal alongside your team rather than managing from a dashboard
- Open to travel up to 20% of the time to meet with buyers and customers
- Use UserGems and AI (Claude Cowork, Codex) to expand team’s capacity and effectiveness
Revenue and pipeline
- Own team quota attainment and hold AEs accountable for outbound sourcing targets
- Drive forecasting accuracy, pipeline health, and revenue predictability
- Engage with key prospects and customers at the executive level to accelerate deals, negotiate, and strengthen relationships - on Zoom and in-person
- Provide feedback from the market (AEs, prospects, customers) to product, engineering, and marketing teams to enhance our product and positioning
Enablement & Process
- Initiate and own projects and process iterations that strengthen team performance to include enablement, new hire ramping, and compensation plans
- Own and evolve commission structure for the team- designing and maintaining plans that reward the right behaviors
- Partner closely with marketing - both teams are measured by revenue, and this alignment is a core part of how we operate
What you've accomplished so far:
- 7+ years in B2B SaaS sales with at least 5 years managing a team of full-cycle AEs
- Proven track record of building, scaling, and leading high-performing teams that consistently exceed revenue targets
- Deep fluency in outbound sales motion for both Commercial and Enterprise segments - you’ve built pipelines, closed deals, and have coached others to do the same
- Built or overhauled sales programs- playbooks, onboarding, training, comp plans- not just inherited
- Strong forecasting and pipeline management using data to drive decisions
- You’ve hired well, ramped AEs quickly, and have a track record of retaining and developing top talent to include front line management
- You’ve thrived in an early stage, high growth environment
Compensation information- target OTE range for this role is $300K- $450K annually, with a 50/50 base/variable split. Final compensation package will be determined based on commensurate experience, qualifications, and demonstrated ability to perform in the role.
Why you should join:
- You’ll be part of a fast-growing startup as it scales from 70 to hundreds of employees
- Customers love us! (see our Customers & Hall of Gems pages)
- Employees love working here (see Repvue & Glassdoor reviews) and stay a long time. Median tenure for Director+ is 5 years and median tenure for all employees is 3+ years.
- We just had our best quarter ever (by >2X) and signed our first 7 digit contract.
- We will be cash-flow positive by the end of the year and can create our own destiny.
- We're a remote-first company with employees across the Americas and Europe
- We have company & department-wide in-person off-sites around the world so that everyone stays connected
- We believe strongly in being customer-focused and data-driven in everything we do
- We value individual differences in the workforce and strive to make everyone feel welcomed and accepted, regardless of their skin color, gender or sexual orientation
- Health benefits & competitive salary
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Lead and grow a Central-region mid-market sales organization targeting employers (50–9,999 lives). Manage Regional Directors and AEs, set and execute sales strategy, develop broker/partner relationships, hit revenue targets, collaborate cross-functionally, and ensure compliance. Coach and scale a high-performing team focused on measurable impact and adoption of AI-enabled tools.
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