Services Sales Executive

CBTS • Chicago, IL

11h • $100,000 - $130,000 • Remote

About The Position

We are seeking a top-performing Services Sales Executive (SSE) to lead and win complex, outcome-based Professional Services engagements across enterprise and high-growth accounts. This is a strategic deal leadership role designed for experienced Professional Services sellers, Customer Practice Managers, and services-led growth leaders from Managed Service Providers (MSPs) and Global Systems Integrators (GSIs).

Operating at the center of the sales cycle, you will own end-to-end deal strategy, solution positioning, and commercial execution — from early customer engagement through signed Statement of Work (SOW) and into successful delivery outcomes. You will partner closely with Account Executives and Account Managers, Solution Leads, Solution Architects, Solution Engineers, Advisory & Strategic Pursuits, and Delivery teams to ensure solutions are compelling, executable, and aligned to customer outcomes.

This role goes beyond traditional selling. You will act as a trusted advisor to both internal account teams and clients, a growth partner to the business, and the orchestrator of cross-functional teams to shape and close high-value transformation programs. While the primary mandate is Professional Services, the north star is guiding clients toward long-term managed services relationships and recurring revenue streams.

Requirements

• 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).

Nice To Haves

• Experience selling across one or more of the following service domains: 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.

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed