Technical Sales Executive – Consulting Services

Location: Chicago - Remote

Compensation: 100% commission; no base salary

About Pearl Consulting Group

Pearl Consulting Group helps organizations deliver complex initiatives across cybersecurity, program and project delivery, organizational change management, and governance, risk, and compliance. We bring together people, process, technology, and communications to help clients implement solutions and make them work in practice.

The opportunity

We’re looking for a sales professional who can win new clients for PCG. This is a hands-on, new-business role for someone who knows how to sell consulting services, build relationships with enterprise decision-makers, and turn an initial conversation into a defined engagement.

PCG is a growing firm, so this role calls for initiative and persistence. You’ll build your own pipeline, pursue opportunities through your network and targeted outreach, and work closely with leadership and delivery teams to shape proposals that address client needs.

What you’ll do

• Identify, prospect, and win new enterprise and upper mid-market clients.
• Build relationships with CISOs, CIOs, technology leaders, transformation leaders, and other decision-makers.
• Lead discovery conversations to understand business challenges, priorities, stakeholders, and buying timelines.
• Position PCG’s consulting capabilities in cybersecurity, change management, program delivery, and GRC.
• Develop opportunities through direct outreach, referrals, events, and partner relationships.
• Collaborate with PCG leadership and delivery experts on solution design, proposals, scopes of work, and presentations.
• Manage opportunities from first conversation through negotiation and signed agreement.
• Maintain accurate pipeline activity and forecasts in HubSpot.
• Help strengthen PCG’s market presence by sharing client insights and identifying opportunities for repeat or expanded work.

What we’re looking for

• Proven success selling consulting or professional services and winning new clients. Experience selling software alone does not meet this requirement.
• Experience developing business with enterprise or upper mid-market organizations.
• A track record of sourcing your own opportunities and managing a full sales cycle.
• The ability to discuss technical and business challenges credibly, ask strong discovery questions, and bring in subject matter experts at the right time.
• Strong executive communication, relationship-building, negotiation, and follow-through.
• Comfort working independently in a growing company where you’ll help create momentum as well as close deals.
• Experience selling cybersecurity, technology transformation, organizational change, or program delivery services is especially valuable. An established network of relevant buyers or partners is a plus.

Compensation

This is a 100% commission role with no base salary. Commission structure, payment terms, and engagement details will be discussed during the interview process.

Who will thrive here

You’re energized by opening doors, building trust, and earning business through thoughtful persistence. You take ownership of your pipeline, move opportunities forward without waiting for a playbook, and know that a strong consulting sale starts with understanding what the client needs to accomplish.