Director, Deal Desk
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-06-28
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Business
Financial Analyst, Operations Manager
Director, Deal Desk
At Flock, our ambition is to scale the business with greater rigor, speed, and consistency across the revenue process. As our sales motions expand across products, segments, and increasingly complex commercial structures, we need a leader who can help the field close the right deals faster while protecting pricing discipline, downstream process integrity, and customer experience.
We are seeking a Director, Deal Desk to lead and mature the Deal Desk function s role will sit at the center of our quote-to-close motion and serve as a strategic partner to Sales, Finance, Legal, Pricing and Packaging, Systems, and Revenue Operations. You will own the operating model that governs complex and non-standard deals, while ensuring the field has the guidance, support, and structure needed to move quickly and consistently.
This is a leadership role for someone who can balance commercial judgment with operational rigor. You should be equally comfortable helping structure a complex deal, setting clear approval guardrails, improving workflows and SLAs, and coaching a team to operate as trusted advisors to the business.
The Skillset10+ years of progressive experience in Deal Desk, Revenue Operations, Sales Operations, Finance, Pricing, or related commercial functions.
3+ years of people leadership experience, including building or leading a high‑performing operational team.
Demonstrated success supporting complex B2B technology or SaaS deal structures in a fast‑moving environment.
Strong judgment in balancing revenue acceleration, pricing discipline, process integrity, and customer outcomes.
Deep familiarity with quoting, approvals, contract structure, and the broader quote‑to‑cash process.
Strong analytical skills and the ability to use data to identify trends, diagnose friction, and improve decision‑making.
Proven ability to influence senior cross‑functional stakeholders without relying on formal authority alone.
Strong executive communication skills and the ability to translate complex tradeoffs into clear recommendations.
Experience with Salesforce and related commercial systems; CPQ experience strongly preferred.
Comfortable operating in ambiguity and shifting between strategic design work and hands‑on problem solving.
Feeling uneasy that you haven't ticked every box? That's okay; we've felt that way too. Studies have shown women and minorities are less likely to apply unless they meet all qualifications. We encourage you to break the status quo and apply to roles that would make you excited to come to work every day.
90 Days at FlockWe prescribe to 90 day plans and believe that good days lead to good weeks, which lead to good months. This serves as a preview of the 90 day plan you will receive if you were to be hired in this role at Flock.
Salary & EquityIn this role, you'll receive a starting salary between $225,000 and $240,000 as well as Flock Stock Options. Base salary is determined by job‑related experience, education/training, as well as market indicators. Your recruiter will discuss this in‑depth with you during our first chat.
LocationWe're building the impossible, together. To drive innovation through in‑person collaboration, we're prioritizing candidates in our key hubs:
Atlanta, Boston, Chicago, Denver, Los Angeles, New York City, San Francisco, and Austin. While we value the energy of our hub communities, we embrace remote work and welcome applications from exceptional talent across the United States.
Flexible PTO
:
We offer non‑accrual PTO, plus 11 company holidays.
Fully‑paid health benefits plan for employees
: including Medical, Dental, and Vision and an HSA match.
Family Leave
:
All employees receive 12 weeks of 100% paid parental leave. Birthing parents are eligible for an additional 6‑8 weeks of physical recovery time.
Fertility & Family Benefits
:
We have partnered with Maven, a complete digital health benefit for starting and raising a family. Flock will provide a $50,000‑lifetime maximum benefit related to eligible adoption, surrogacy, or fertility expenses.
Spring Health
:
Spring Health offers a variety of mental health benefits, including therapy, coaching, medication…
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