Deal Maker (Large Enterprise Deals)

Peskind Executive Search, Inc.; United States; Hybrid; USD 180,000 - 340,000; Full time

Benefits offered by this job

Competitive compensation

Career advancement

Flexible remote/hybrid work

Well-being programs

Professional development

Job summary

Peskind Executive Search, Inc. is seeking a Deal Maker to lead and close large, complex enterprise deals ($25M+), partnering with client executives to drive outcomes across strategic accounts.

You will own high-value pursuits from early qualification through contract signature, coordinating with internal executives and client stakeholders for success. The role focuses on building executive-level relationships, crafting winning deal strategies, and negotiating favorable commercial terms while

Qualifications

• Bachelor’s degree or equivalent experience.
• 6–8+ years of IT services, consulting, or digital transformation sales, ideally with experience closing large enterprise deals.

Responsibilities

• Own and lead large, complex deals ($25M+) from qualification through contract signature.
• Build deep understanding of client drivers and decision processes.
• Identify opportunities within accounts and expand relationships.
• Apply a consultative approach to recommend solutions aligned to client objectives.
• Assemble and guide cross-functional pursuit teams.
• Develop a clear win strategy and navigate governance for approvals.
• Maintain executive relationships from C-Suite to operations.
• Negotiate contracts that optimize profitability and reduce risk.
• Drive high win rates and ensure smooth transition to delivery.

Skills

Executive presence

Strategic selling

Negotiation

Account planning

Education

Bachelor’s degree or equivalent

Job description

Deal Maker – Large Enterprise Deals**

Peskind Executive Search has been engaged by a global technology and services organization to identify a Deal Maker to lead and close large, complex enterprise deals (typically $25M+) across strategic accounts. This individual will own high-value pursuits from early qualification through contract signature, partnering closely with internal executives and client stakeholders to drive successful outcomes.

Role Overview

The Deal Maker will shape and lead major pursuits, develop deep client insight, and assemble the right pursuit team to deliver competitive and compelling proposals. This role focuses on building strong executive-level relationships, understanding organizational priorities, crafting winning deal strategies, and negotiating favorable commercial terms. You will serve as the chief orchestrator across the full pursuit lifecycle.

Key Responsibilities

• Own and lead large, complex deals ($25M+) from qualification through contract signature.

• Build deep understanding of client business drivers, requirements, and decision processes.

• Identify new opportunities within assigned accounts while expanding existing relationships.

• Utilize a consultative approach to recommend solutions aligned to client objectives.

• Assemble, motivate, and guide cross-functional pursuit teams.

• Develop and articulate a clear, differentiated win strategy throughout the client’s RFP/selection process.

• Navigate internal governance processes to secure alignment and approvals.

• Maintain strong relationships across client organizations, from C-Suite to operational teams.

• Track competitive positioning and adapt strategies to maximize win probability.

• Re-qualify deals continuously and maintain accurate sales forecasting and CRM hygiene.

• Negotiate contracts that optimize profitability while reducing commercial risk.

• Drive high win rates and ensure successful transitions into delivery.

Competencies & Behaviors

• High integrity, ethical decision-making, and strong executive presence.

• Client-centric relationship builder with exceptional communication skills.

• Strategic thinker with strong business and account planning capability.

• Proven ability to lead teams through complex, high-stakes sales cycles.

• Commercially sharp, innovative, and entrepreneurial mindset.

• Skilled negotiator with the ability to influence at all levels.

• Advocates diversity, continuous learning, and environmentally responsible business practices.

Qualifications

• Bachelor’s degree or equivalent experience.

• 6–8+ years of IT services, consulting, or digital transformation sales, ideally with experience closing large enterprise deals.

Rewards & Benefits

• Competitive compensation structure tied to large-deal performance.

• Opportunities for career advancement within a global organization.

• Flexible remote/hybrid work options.

• Well-being, professional development, and continuous learning programs.

• Access to a broad benefits platform, including culture, wellness, and charitable initiatives.