VP Sales, North America

Overview

You run the North America sales organization for Litmos, a 222-person LMS company. You manage frontline sales leaders who oversee AEs and SDRs selling learning management software to mid-market and enterprise companies. Your job is to hit the revenue target, build a predictable pipeline, and improve win rates in a competitive LMS market.

Role Snapshot

Company Context

Stage: Growth stage (222 employees, established product)

Size: 222 employees

Growth: CRO brought in to scale, actively hiring VP and SVP roles for next phase

Market Position: Established player in crowded LMS market - competing against newer platforms and legacy systems

GTM Reality

Pipeline Sources:

• 40% Inbound - MQLs from website demos, content downloads, free trial signups (quality varies)
• 50% Outbound - Reps cold calling and emailing L&D leaders, HR VPs, training directors
• 10% Partners/Referrals - Some channel motion, customer referrals

SDR/AE Structure: Likely has dedicated SDR team feeding AEs, but may need restructuring

SE Support: Sales Engineers support on technical demos and POCs for larger deals

Competitive Landscape

Main Competitors: Likely competing against Docebo, TalentLMS, Absorb LMS, plus legacy systems like Cornerstone and SumTotal

How They Differentiate: "Speed to value" positioning - easy to use, AI/automation features, comprehensive content library

Common Objections: "We already have an LMS," implementation concerns, content quality questions, integration complexity

Win Themes: Ease of use vs legacy systems, better UX than competitors, strong content library, speed of deployment

What You'll Actually Do

Time Breakdown

Team Management (30%) | Strategic Planning (25%) | Deal Reviews (20%) | Executive Alignment (15%) | Forecasting (10%)

Key Activities

• Weekly 1:1s and Pipeline Reviews: You spend 6-8 hours per week reviewing deals with your sales managers, pressure-testing forecasts, and identifying where reps are stuck. A lot of deals slip because L&D projects get deprioritized.
• Hiring and Team Building: You're probably inheriting a team that needs upgrading. You'll spend time recruiting senior AEs who can run enterprise cycles and potentially restructuring territories or segments.
• Sales Process and Methodology: The CRO wants "disciplined growth" which means you're implementing (or fixing) their sales methodology, deal stages, qualification criteria, and forecasting rigor. Expect resistance from reps used to doing it their own way.
• Strategic Account Planning: You work with marketing and the CRO on account-based strategies for target accounts, vertical plays, and competitive takeouts. You're translating strategy into executable plays for your team.
• Board Prep and QBRs: You own the North America revenue story for board decks and quarterly business reviews. When the number is off, you're explaining why and what's being done about it.

The Honest Reality

What's Hard

• LMS market is saturated: Most prospects already have something. You're fighting inertia and the "good enough" problem. Reps need to be skilled at competitive displacement and change management selling.
• Long, consensus-driven sales cycles: L&D, HR, IT, procurement, and sometimes compliance all have a say. Deals drag out and slip quarters constantly. Your forecast accuracy will be scrutinized.
• Team performance variability: You'll likely inherit some reps who can't execute at the level needed. Tough conversations and potential turnover are part of year one.
• CRO expects fast results: Mark is building his leadership team and needs wins. Pressure to show improved metrics quickly while also building sustainable systems.
• Internal alignment challenges: Sales, marketing, product, and CS don't always agree on ICP, messaging, or prioritization. You spend time in meetings aligning cross-functionally.

What Success Looks Like

• Hitting 95%+ of quarterly revenue targets consistently
• Improving win rate by 10-15% in first year through better qualification and deal execution
• Building a pipeline that's 4-5x quota with clean, accurate forecasting
• Reducing sales cycle length by optimizing the sales process and removing internal friction
• Developing 2-3 sales leaders on your team who could eventually run their own regions

Who You're Selling To

Primary Buyers:

• VP/Director of Learning & Development (main champion)
• CHRO or VP Human Resources (budget holder)
• IT Director (technical evaluation, integrations)
• Procurement (contracts, pricing)

What They Care About:

• Ease of implementation and speed to launch
• User adoption rates and learner experience
• Content quality and breadth (off-the-shelf training library)
• Integration with existing HRIS, CRM, and content authoring tools
• Reporting and compliance tracking (especially in regulated industries)
• Total cost of ownership vs current solution

Requirements

• 10+ years in B2B SaaS sales with 5+ years leading sales teams (managers of managers experience required)
• Track record of building and scaling sales organizations that consistently hit targets
• Experience selling into HR/L&D buyers and navigating complex enterprise sales cycles
• Strong understanding of sales metrics, forecasting, and pipeline management
• Player-coach mentality - willing to jump into key deals while developing your team
• Experience implementing sales methodologies (MEDDIC, Command of the Message, etc.)
• Comfortable in a scale-up environment where you need to build and refine processes
• East Coast based strongly preferred (likely for customer concentration and team location)
• Ability to partner with CRO and exec team on strategic GTM decisions