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Services Sales Executive

OnX
Chicago, USA
Full-time
Senior Level
Hybrid
USD 100000-130000 yearly
Discovered 1 weeks ago
Free

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  • Proactively identify, create, qualify, and lead large, complex Professional Services opportunities ($5M–$50M+) across existing accounts, whitespace segments, and targeted new logos.
  • Engage early with customers alongside Account Executives and Account Managers to shape demand, define transformation agendas, and uncover business-outcome-led opportunities.
  • Lead consultative, outcome-based discovery sessions aligned to business priorities and strategic objectives.
  • Own and drive the end-to-end sales cycle from initial engagement through close.
  • Align with Account Executives and regional sellers on territory strategy, whitespace penetration, account plans, and customer engagement priorities.
  • Consistently generate pipeline through outbound prospecting, relationship development, referrals, and strategic account penetration.
  • Collaborate with Solution Leads to define overall solution strategy and approach.
  • Partner with Solution Architects to design scalable, fit-for-purpose solutions and with Solution Engineers to validate feasibility and supporting detail.
  • Collaborate with Advisory & Strategic Pursuits for multi-workstream strategic opportunities.
  • Work closely with Delivery teams to ensure executability and alignment to capability.
  • Translate customer needs into outcome-based service offerings — including advisory and strategy engagements, assessments and workshops, implementation and transformation programs, and managed services.
  • Lead proposal development, pricing strategy, and commercial structuring — ensuring proposals are compelling and clearly articulate how we solve for customer challenges and deliver measurable business outcomes.
  • Partner closely with technical presales, architects, and delivery leaders to identify, articulate, and refine solution design into clear, accurate, and compelling customer-facing proposals.
  • Drive internal alignment and approvals to accelerate time-to-close.
  • Build and maintain trusted relationships with C-suite and senior business stakeholders.
  • Act as a trusted advisor to Account Managers and Account Executives, guiding customers through complex decisions with clarity and confidence.
  • Lead executive-level conversations focused on business impact — not just technology.
  • Navigate complex stakeholder environments to drive alignment and consensus.
  • Own deal quality, margin, and commercial viability across every pursuit.
  • Build and maintain a robust pipeline of Professional Services opportunities across existing accounts, whitespace segments, and new logos.
  • Drive pipeline creation, account expansion, and whitespace penetration.
  • Identify and convert follow-on, cross-sell, and managed services opportunities — positioning Professional Services engagements as the gateway to long-term recurring revenue.
  • Balance customer value with profitable growth and commercial rigor.
  • Achieve monthly and annual gross profit, bookings, and pipeline creation targets.
  • Maintain executive-level visibility into active engagements sold.
  • Act as the escalation point for critical risks and customer concerns.
  • Ensure fidelity of original business goals, intent, commitments, and scope through delivery and managed services phases.
  • Feed insights back into future deals, offerings, and go-to-market strategy.
  • Develop repeatable sales plays, solution frameworks, and go-to-market assets.
  • Mentor Solution Leads, Architects, and Engineers on deal strategy and positioning.
  • Bring market insight, competitive intelligence, and client feedback to shape portfolio evolution.
  • 10–15+ years in enterprise services sales, consulting, or services-led environments.
  • 5+ years selling outcome-based Professional Services via Statement of Work (SOW).
  • Proven success leading large, complex deals ($5M–$50M+) from inception through close.
  • Proven experience personally owning and drafting customer-facing SOWs for complex services engagements.
  • Demonstrated success partnering with technical presales teams to scope and close services opportunities.
  • Background in MSP, GSI, or large-scale consulting organizations with deep experience across sales, presales, and delivery collaboration models.
  • Strong track record in consultative, outcome-based, and value-led selling.
  • Expertise in commercial structuring, pricing strategy, and negotiation.
  • Proven ability to connect technology investments to business outcomes and ROI.
  • Proven history of meeting or exceeding revenue and gross profit quotas.
  • Experience prospecting into enterprise and mid-market accounts.
  • CRM discipline (Salesforce preferred).
  • Cloud & Infrastructure Services.
  • Application Modernization and Software Development.
  • Data & AI Services.
  • Cybersecurity Services.
  • Unified Communications and Collaboration.
  • Understanding of services delivery models (project-based and managed services), transformation programs, and enterprise IT operating models.
  • Demonstrated success building and closing multi-year transformation programs.
  • Experience working in matrixed organizations across technology or services domains.
  • Deal Leadership: Owns and drives complex pursuits from inception to close with confidence and precision.
  • Executive Presence: Trusted advisor at the C-level who leads with credibility and influence.
  • Commercial Acumen: Balances value creation with profitability — pricing, margin, and deal structuring are second nature.
  • Outcome Orientation: Anchors all conversations in measurable business impact, not just technology.
  • Orchestration Excellence: Aligns diverse teams — Solution Leads, Architects, Engineers, Delivery, and partners — into a single, winning strategy.
  • Strategic Thinking: Connects individual deals to long-term account growth while maintaining a sharp understanding of current market conditions and technology advancements.
  • Market Awareness: Stays current on industry trends, competitive dynamics, and emerging technologies to sharpen pursuit differentiation.
  • Shape enterprise transformation agendas.
  • Influence multi-million-dollar investment decisions.
  • Lead end-to-end services pursuits.
  • Build long-term client partnerships and growth platforms.
  • Stay engaged post-sale to protect outcomes and expand growth.
  • Competitive base salary and performance-based incentive plan tied to bookings and gross profit contribution.
  • Opportunity to shape high-visibility, high-value strategic pursuits and leave a lasting mark on client transformation journeys.
  • Access to a best-in-class partner ecosystem including co-sell programs and joint go-to-market resources.
  • Dedicated professional development budget covering certifications, industry conferences, and advanced training.
  • Collaborative team culture that shares assets, wins, and knowledge across a growing community of services professionals.

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