Head of Sales

Head of Sales
USA Remote

• Salary: $175,000-$225,000

We help organizations modernize their businesses through enterprise technology, advisory services, implementation, managed services, and long-term customer partnerships.


We are evolving from a traditional ERP reseller and services organization into a modern business-transformation partner-one that sells outcomes rather than products or hours, uses AI and automation aggressively, and remains accountable for customer value beyond the initial sale.


Our goal is to build a scalable growth platform that creates successful customers, generates recurring revenue, and produces genuine "Raving Fans."


THE OPPORTUNITY:

• We are seeking a Head of Sales to lead the next stage of our commercial transformation
• This is a hands-on, player-coach leadership role. The Head of Sales will own new-business results, develop the sales team, strengthen our go-to-market system, and personally participate in strategically important opportunities
• The ideal leader brings discipline without bureaucracy, urgency without chaos, and accountability without fear. You should be comfortable in an entrepreneurial environment where systems are still maturing and success requires both strategic leadership and hands-on execution

KEY RESPONSIBILITIES:
Build a Predictable Growth Engine

• Own new-logo bookings, revenue, pipeline, conversion, and forecast accuracy
• Translate company objectives into focused territory, account, and pipeline plans
• Establish a consistent cadence for pipeline inspection, forecasting, deal strategy, and performance management
• Improve pipeline quality, coverage, velocity, and conversion
• Ensure significant opportunities have a clearly defined business problem, value proposition, urgency, decision process, buying committee, competitive strategy, and next step

Lead From the Front

• Personally participate in prospecting, discovery, executive meetings, deal strategy, proposals, negotiations, and closing
• Help navigate complex, long-cycle ERP and business-transformation opportunities
• Build trusted relationships with customer executives and serve as a credible business advisor
• Model strong preparation, discovery, follow-up, commercial judgment, and closing discipline

Modernize How We Sell

• Shift conversations from products, functionality, and billable hours to business problems, risk, value, and measurable outcomes
• Help customers clearly articulate Why change? Why now? What value will the investment create?
• Position ERP as part of a broader business transformation rather than simply a technology replacement
• Develop modern commercial offerings, including advisory services, assessments, roadmaps, packaged solutions, recurring services, and outcome-oriented engagements
• Use AI, automation, data, and modern technology to improve prospecting, account planning, opportunity management, coaching, and forecasting

Build a Team-Selling Culture

• Coordinate sales, marketing, solution architecture, delivery, managed services, customer success, executives, and subject-matter experts around the customer
• Build relationships across the buying committee rather than relying on a single champion
• Establish clear roles, preparation, ownership, and follow-up for important customer interactions
• Connect the initial sale to implementation success, managed services, expansion, and long-term customer relationships

Develop the Sales Organization

• Set clear expectations for territory ownership, pipeline development, opportunity progression, closing, and accountability
• Coach sellers through live opportunities, not just retrospective performance reviews
• Assess individual strengths and gaps and create targeted development plans
• Recruit, onboard, develop, and retain high-performing sales talent
• Address underperformance directly, fairly, and promptly
• Build a culture where feedback is candid, commitments matter, and people own their results

Connect Sales With Customer Success

• Set realistic expectations and ensure a strong transition from selling to implementation and ongoing service
• Protect margin and avoid poorly qualified, poorly scoped, or structurally unhealthy business
• Use delivery and customer feedback to improve qualification and selling
• Help create referenceable customers, recurring revenue, and expansion opportunities

HOW SUCCESS WILL BE MEASURED:
Success will be measured by both commercial results and the strength of the sales system being built:

• New-logo bookings and revenue
• Qualified pipeline creation and coverage
• Win rate and stage-to-stage conversion
• Sales-cycle length and opportunity velocity
• Forecast accuracy
• Average deal size and gross-margin quality
• Executive-level and multi-threaded customer relationships
• Managed-services and recurring-revenue attachment
• Seller productivity and accountability
• Quality of the sales-to-delivery transition
• Customer reference ability and expansion

THE LEADERSHIP PROFILE:
The ideal candidate is:

• A proven sales leader who still loves selling and working directly with the team
• Experienced in complex enterprise technology, ERP, consulting, managed services, or transformation sales
• Comfortable selling to CEOs, CFOs, CIOs, COOs, and cross-functional buying committees
• Able to translate complex technology into a clear, financially relevant business case
• Strong in both pipeline creation and opportunity conversion
• A disciplined qualifier who understands that interest is not the same as a qualified opportunity
• Skilled at challenging customers constructively while remaining curious, humble, and attentive
• Commercially disciplined and committed to protecting margin, scope integrity, and delivery success
• An effective coach who can raise performance while maintaining trust and motivation
• Comfortable making difficult talent and opportunity decisions
• Accountable, collaborative, candid, resilient, and low ego
• Energized by building and transformation rather than dependent on mature systems or abundant inbound demand

PREFERRED EXPERIENCE:

• Proven success leading and personally closing complex B2B technology or professional-services opportunities
• Experience managing quota-carrying sellers with territory responsibility
• A track record of building pipeline where demand must be created rather than simply processed
• Experience implementing sales methodologies, forecasting disciplines, qualification standards, and performance-management systems
• Familiarity with ERP, enterprise applications, manufacturing, aerospace and defense, construction, or asset-intensive industries
• Experience developing recurring-revenue, managed-services, advisory, or packaged-service offerings
• A track record of improving coordination across sales, marketing, delivery, and customer success

WHAT THIS ROLE IS NOT:
This is not a role for someone who:

• Reports on pipeline rather than changing it
• Depends on marketing or partners to generate all meaningful opportunities
• Confuses activity with progress or optimism with forecast evidence
• Operates as an individual hero rather than building a coordinated selling system
• Sells whatever the customer will buy and leaves delivery to manage the consequences
• Avoids accountability, difficult feedback, or direct involvement in challenging deals

WHY JOIN OUR TEAM:

• The right leader will have meaningful influence over our sales strategy, talent, offerings, market positioning, customer experience, and future growth model

We are looking for more than someone to inherit and administer a sales team. We want a leader who will help build a disciplined, modern, AI-enabled commercial organization that wins through expertise, teamwork, customer outcomes, and accountability-and who is prepared to lead, sell, coach, and own the result.


We are an equal opportunity employer, and we are an organization that values diversity. We welcome applications from all qualified candidates, including minorities and persons with disabilities.


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