Deal Operations Manager

Sierra; London (KY); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Unlimited PTO

Medical, dental, and vision

Life insurance

Disability benefits

Retirement plan

Parental leave

Fertility benefits (Carrot)

Lunch and snacks

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is seeking a Deal Operations Manager to sit at the intersection of Sales, Finance, Legal, and Product. You will structure, price, and close complex enterprise deals, acting as the backbone of our sales motion from proposal to signature.

In this role you will design deal desk processes, implement discounting guardrails, and manage matrices that balance speed with governance. You will build dashboards, track metrics, and optimize revenue recognition across multi-year engagements.

Qualifications

• 3+ years in deal desk, sales operations or revenue operations.
• Strong Excel/Google Sheets skills and financial modeling.
• Experience with CRM platforms (Salesforce preferred) and contract/CLM tools.

Responsibilities

• Own end-to-end deal support: structuring pricing, building proposals, and running approval workflows.
• Partner with Sales to design and maintain deal desk processes, discounting guardrails, and approval matrices.
• Work cross-functionally with Legal, Finance, and Product to unblock non-standard terms and multi-year/multi-product deals.
• Build and maintain tools/dashboards to track deal pipeline, cycle time, and win/loss trends.
• Analyze deal data to identify bottlenecks and recommend process improvements.
• Support quote-to-cash processes, ensuring contract terms and revenue recognition handoffs are accurate.
• Own special projects related to pricing strategy, packaging, and international deal structures.
• Leverage AI-native tools to automate deal workflows and scale systems.

Skills

Deal desk

Sales operations

Financial modeling

CRM (Salesforce)

Contract/CLM tools

Data analysis

Communication

Tools

Salesforce

Ironclad

DocuSign

Google Sheets

Job description

About us

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

About the Role

We're looking for a Deal Operations Manager to sit at the intersection of Sales, Finance, Legal, and Product, helping structure, price, and close complex enterprise deals. You'll be the operational backbone of our sales motion — ensuring deals move quickly, accurately, and profitably from proposal to signature.

What you'll do

• Own end-to-end deal support: structuring pricing, building proposals, and running approval workflows for enterprise and strategic deals.

• Partner with Sales to design and maintain deal desk processes, discounting guardrails, and approval matrices that balance speed with governance.

• Work cross-functionally with Legal, Finance, and Product to unblock non-standard terms, custom packaging, and multi-year/multi-product deals.

• Build and maintain tools/dashboards (Salesforce, Sheets, or internal systems) to track deal pipeline, cycle time, and win/loss trends.

• Analyze deal data to identify bottlenecks in the sales cycle and recommend process improvements.

• Support quote-to-cash processes, ensuring accuracy in contract terms, billing setup, and revenue recognition handoffs.

• Own special projects related to pricing strategy, packaging, discounting policy, and international deal structures.

• Leverage AI-native tools (e.g., Claude Code, Cursor) to automate repetitive deal workflows and create scalable systems.

What you'll bring

• 3+ years of experience in deal desk, sales operations, revenue operations, or management consulting.

• Strong Excel/Google Sheets skills; comfort with financial modeling and deal economics (discounting, margin, ARR impact).

• Experience with CRM platforms (Salesforce preferred) and contract/CLM tools (e.g., Ironclad, DocuSign).

• High attention to detail — you catch pricing errors and contract inconsistencies before they become problems.

• Ability to manage multiple live deals simultaneously under time pressure without sacrificing accuracy.

• Strong written and verbal communication skills; comfortable presenting recommendations to Sales leadership and executives.

• A proactive, builder mentality — comfortable creating process from scratch in an ambiguous, fast-moving environment.

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

• Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

• Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.

• Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

• Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.

What we offer

We want our benefits to reflect our values and offer the following to full-time employees:

• Flexible (unlimited) paid time off

• Medical, dental, and vision benefits for you and your family

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• Parental leave

• Fertility and family building benefits through Carrot

• Lunch, as well as delicious snacks and coffee to keep you energized

• Discretionary benefit stipend giving people the ability to spend where it matters most

• Free alphorn lessons

These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

Be you, with us

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.