VP of Sales

EasyLlama is transforming the HR compliance industry by reinventing outdated and uninspiring training solutions and adapting them for the mobile-first generation. Our engaging, fun, and interactive training helps millions of employees worldwide build a safer, more positive, and inclusive workplace. As we continue to set the standard in compliance solutions, our vision extends far beyond training—we aim to partner with thousands of organizations to reduce employee risk and foster a more inclusive and secure environment for all.

With world-class customer reviews—boasting a 96% rating on G2 from over 100 reviews—and industry-leading NPS and Customer Satisfaction scores, EasyLlama is proud to have earned the trust of over 5,000 clients, including brands like Shake Shack, WeightWatchers, Sephora, JiffyLube, and Y Combinator. Our mobile-friendly platform delivers on-demand, self-paced, and bite-sized solutions that meet employees where they are, increasing engagement and retention.

At EasyLlama, we are not just transforming compliance training—we are challenging the status quo. We have a strong culture of collaboration, innovation, and getting things done.

About the Role

We’re seeking a strategic, data-driven, and execution-oriented Vice President of Sales to lead EasyLlama's next phase of growth as we scale to $100M+ in recurring revenue. You’ll be responsible for building and optimizing a high-performing sales team, owning sales motions across inbound, outbound, and product-led growth (PLG) strategies. You’ll bring strong “sales math” fundamentals, partner cross-functionally to improve funnel efficiency, and drive GTM execution for our multi-product roadmap.

What You'll Do

• Team Leadership & Coaching: Hire, ramp, and develop top-tier AEs. Build a coaching-driven culture focused on productivity benchmarks, pipeline discipline, and quota attainment.

• Segmented Sales Strategy: Execute differentiated sales motions for SMB, Mid-Market and Enterprise, aligning tactics with ICPs, company size, buyer persona, and product suite.

• PLG & Signal-Based Sales Execution: Operationalize product-led and signal-based selling; enable reps to act on PQLs and usage insights.

• Sales Math & Funnel Modeling: Define and manage KPIs across funnel stages (e.g., MQL→SQL→Closed Won); build dashboards to track rep efficiency and CAC metrics.

• Forecasting & Deal Management: Build and run a disciplined forecast process with pipeline hygiene, regular deal reviews, and forecast accuracy within ±10%.

• Outbound & Partner Strategy: Launch outbound prospecting and partner-influenced motions with playbooks, KPIs, and team execution frameworks.

• Onboarding & Enablement: Create structured onboarding and 30-60-90 ramp plans using our LMS and enablement tools to reduce time-to-productivity.

• GTM Collaboration: Partner with Product and Marketing to align messaging, launch multi-product sales enablement, and support new product introductions.

• ICP & VoB Insights: Own win/loss analysis and continuously refine ICP definitions with data-driven insights across segments and product lines.

• Sales Efficiency & Automation: Work with RevOps to streamline sales workflows, automate reporting, and optimize HubSpot usage.

• External Representation: Represent EasyLlama with strategic prospects, at industry events, and in partner/channel ecosystems.

Who You Are

• 7+ years of B2B SaaS sales leadership, with a track record as a quota-carrying rep and progression into team leadership.

• Experience scaling a sales team from ~$20M to $100M+ in ARR.

• Deep expertise in SMB and Mid-Market sales (up to 5,000 employees).

• Strong grasp of sales math: lead conversion, rep productivity, CAC payback, pipeline coverage, ramp modeling.

• Hands-on experience in PLG and signal-based sales motions, including selling into usage or product-qualified leads.

• Proven operator with pipeline rigor, CRM discipline, and RevOps collaboration.

• Collaborative mindset and experience aligning sales closely with marketing and product.

• High EQ leader with a coaching mentality and strong communication skills.

• Thrives in a fast-paced, high-growth environment with strong ownership and execution focus.

What to Expect

Here's what the interview process looks like:

• Screening interview w/People and Culture leader

• Hiring Manager Interview w/CEO

• Executive Interview w/VP of Marketing

• Peer Interview w/Fractional VP of Sales

• Assessment Interview w/CEO & Sr. AE

How We'll Take Care of You

• Flexible, fully remote environment

• 4 Weeks PTO - Recharging is essential. We respect your time off and encourage it.

• Competitive employer-sponsored health insurances

• 401(k) + company matching

• Professional development reimbursements

• Quarterly remote work benefit

The EasyLlama herd is fully remote, with employees distributed across the US. We are currently hiring in the following approved* states:

AR - Arkansas
CA - California
CO - Colorado
FL - Florida
IL - Illinois
MA - Massachusetts
MN - Minnesota
NE - Nebraska
NJ - New Jersey
NY - New York
NC - North Carolina
OH - Ohio
PA - Pennsylvania
TN - Tennessee
TX - Texas
UT - Utah
VA - Virginia
WA - Washington
WI - Wisconsin

*EasyLlama reserves the right to change the list of approved states at anytime.

To ensure the best employee experience, we offer competitive compensation packages, comprehensive benefits, an annual wellness stipend, PTO, 401k with company matching, and monthly team events to nurture connection!

At EasyLlama, we strive to walk the walk. We are helping make workplaces all over the globe safer and more inclusive, including our own. We honor employees and candidates from all walks of life and all experiences, regardless of race, ethnicity, veteran status, disability, sexual orientation, gender identity or religion.