About the Role
We are seeking a highly experienced Senior Manager, Deal Desk to serve as a key business partner for our enterprise sales organization. In this role, you will oversee the entire deal lifecycle—from initial structuring to final pricing approvals—collaborating closely with Sales, Finance, Legal, and Product stakeholders to accelerate revenue while upholding global commercial standards. This position requires a seasoned expert in enterprise technology transactions who can deliver the strategic judgment and operational structure necessary for complex, high-value deals.
Core Responsibilities
- Act as the commercial advisor for enterprise sales, managing complex deal structuring, pricing methodologies, and compliance for non-standard terms.
- Facilitate cross-departmental deal evaluations with Legal, Finance, and Executive teams for high-priority strategic opportunities.
- Develop and update pricing models and discount policies to balance market competitiveness with corporate margin goals.
- Collaborate with Revenue Operations to improve sales velocity and win rates through streamlined approval workflows and proactive guidance.
- Evaluate market intelligence and internal pricing trends to mitigate revenue loss and improve global commercial strategy.
- Provide support on day to day use of CPQ tools and approval workflows to drive operational efficiency.
- Enforce global commercial policies and escalation protocols to ensure organizational consistency across all regions.
Key Responsibilities
- Serve as a primary business partner for sales supporting complex Enterprise deal structuring, pricing strategies, policy compliance, and oversight to any exceptions to non-standard commercial terms
- Help develop and refine pricing frameworks, discount governance policies, and deal approval workflows that balance competitive agility with margin discipline
- Partner with Sales & Revenue Operations leadership to drive deal velocity, improve win rates, and shorten sales cycles through proactive commercial guidance
- Lead cross-functional deal reviews involving Finance, Legal, Product, and Executive stakeholders for strategic and high-value opportunities
- Analyze deal trends, pricing patterns, and competitive intelligence to continuously refine commercial strategy and identify potential revenue leakage
- Support the build-out and optimization of Deal Desk tooling, CPQ (Configure Price Quote) systems, and approval automation in partnership with Revenue Operations
- Enforce commercial policies and escalation thresholds, ensuring consistency and compliance across sales teams
- Collaborate with regional Sales and Finance leaders to adapt global commercial frameworks to align with industry vertical trends and local market dynamics
Qualifications
- 8+ years of progressive experience in Deal Desk, Sales Operations, Revenue Operations, or Commercial Finance within enterprise B2B technology companies (SaaS, AI, cloud infrastructure, or software)
- Deep expertise in enterprise pricing strategy, discounting frameworks, and complex contract structures (multi-year, multi-product, consumption-based, and subscription models)
- Proven track record operating in a global capacity, supporting sales teams across multiple regions and time zones
- Strong command of CPQ platforms (e.g., Salesforce CPQ, Apttus/Conga, Oracle CPQ) and CRM systems
- Exceptional ability to build cross-functional relationships and influence without authority, including at the executive level
- Analytical rigor combined with sound business judgment — able to move quickly on complex deals without sacrificing commercial integrity
- Experience navigating and structuring multi-million dollar enterprise transactions with C-suite-level stakeholders
- Bachelor's degree required; MBA or equivalent business experience preferred
What Sets the Ideal Candidate Apart
- Proven ability to scale Deal Desk operations through critical growth phases within various organizational environments, including Series C+ startups and established technology firms entering new markets.
- Familiarity with international commercial compliance, multi-currency pricing, and cross-border contracting nuances
- Background working alongside Product-Led Growth (PLG) and Consumption-Based Pricing models in addition to traditional SaaS licensing / subscription models
Pay Range (Base Pay): $115,000 - $175,000
Other Types of Pay: Based on level and role the employee may be eligible for long term incentives in the form of equity and short term incentives of either bonus or commission.
Health Insurance: Medical, Dental, Vision, Life and Disability Insurance, Employee Assistance Program (EAP).
Retirement Benefits: 401(k) plan
Paid Time Off: Talkdesk offers an uncapped paid time off program, subject to manager approval and consistent with business needs.
Paid Holidays: Talkdesk offers 14 paid holidays each year.
Paid Sick Leave: Employees have uncapped paid time off, subject to manager approval and consistent with business needs.
Method of Application: Apply online.
Application Window: The application window is expected to close at least 5 days from the posting date. The application was posted on 06/09/2026.
All questions or concerns about this posting should be directed to the Talent team at [email protected].
Talkdesk is pioneering a new era of Customer Experience Automation (CXA), redefining how the world’s most admired brands interact with their customers through AI. Our global team of courageous innovators is customer-obsessed, building AI-first solutions that put empathy, trust, and transparency at the center of every interaction. We foster an inclusive culture where diverse perspectives drive our success and every voice belongs. Combining the stability of a global leader with the agility of a disruptor, Talkdeskers are empowered with the autonomy to drive meaningful impact, while giving back to the communities and environment around us.
Talkdesk has been recognized as a Leader in the Gartner® Magic Quadrant™ for Contact Center as a Service (CCaaS) and in the G2 Overall Grid® Reports for AI Agents and Contact Center. With seven consecutive years on the Forbes Cloud 100 and multiple AI Breakthrough awards, there has never been a more exciting time to join us as we shape the future of customer experience automation!
Work Environment and Physical Requirements:
Primarily office-environment work, extended periods of sitting or standing, computer-based work. Limited lifting, and equipment usage limited to computer-related equipment (keyboards, mouse, etc.)
The Talkdesk story hinges on empathy and acceptance. It is the shared goal among all Talkdeskers to empower a new kind of customer hero through our innovative software solution, and we firmly believe that the best path to success for our mission is inclusivity, diversity, and genuine acceptance. To that end, we will hire, promote, work along, cheer for, bond with, and warmly welcome into the Talkdesk family all persons without regard to ethnic and racial identity, indigenous heritage, national origin, religion, gender, gender identity, gender expression, sexual orientation, age, disability, marital status, veteran status, genetic information, or any other legally protected status.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
