Cresta

Deal Strategy & Operations Manager

Cresta$140K — $175K *
US-AnywhereRemote in United States
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in Deal Desk, Deal Strategy, Commercial Operations, Revenue Operations, Legal Ops, or Sales Operations
  • Experience managing complex enterprise SaaS deals throughout the lifecycle
  • Proficiency with CPQ tools, specifically Subskribe is preferred
  • Strong expertise in Salesforce for quoting and reporting
  • Knowledge of enterprise SaaS contracting (MSA, DPA, SOW)
  • Excellent communication skills and emotional intelligence
  • Ability to navigate ambiguity in fast-paced settings

Responsibilities

  • Collaborate with Sales teams to structure high-value enterprise transactions
  • Develop creative pricing models and commercial terms to enhance customer experience
  • Manage approval workflows and act as escalation point from quote to signature
  • Convert deal data and trends into actionable insights
  • Conduct win/loss reviews to refine deal strategy
  • Ensure compliance with revenue recognition principles
  • Drive improvements across the quote-to-cash process

Benefits

  • Variety of medical, dental, and vision plans
  • Paid parental leave for family support
  • Monthly Health & Wellness allowance
  • Work from home office stipend
  • Lunch reimbursement for in-office employees
  • Flexible Paid Time Off (PTO)
Full Job Description
About the Role:

Cresta is seeking a Deal Strategy & Operations Manager to serve as a senior individual contributor and strategic partner on our Commercial Strategy & Operations team. This role owns the strategy and execution of Cresta's most complex, non-standard enterprise deals, acting as the quarterback from quote to close.

Reporting to Lauren Jungers, Sr. Director of Commercial Strategy & Operations, this role works closely with Sales leadership, Finance, Legal, Security, and RevOps to structure deals that accelerate revenue while protecting Cresta's long-term business interests.

This is an individual contributor role (no direct people management).
What You'll Do

Deal Strategy & Execution
  • Partner with US and international Sales teams to architect and execute complex, high-value enterprise transactions
  • Build creative deal structures, pricing models, and commercial terms that balance speed, risk, margin, and customer experience
  • Own approval workflows and act as escalation owner from first quote through final signature
  • Translate deal data, discount trends, and outcomes into actionable insights
  • Lead win/loss and deal retrospectives to institutionalize learnings and refine deal strategy
  • Ensure deal structures align with revenue recognition principles and company financial goals

Process & Systems Modernization
  • Drive end-to-end improvements across the quote-to-cash lifecycle
  • Define business requirements and partner with systems teams on Subskribe, CLM, and Salesforce enhancements
  • Lead UAT and rollout of new deal processes and tooling
  • Represent Deal Strategy & Operations as a key stakeholder on high-priority cross-functional initiatives
  • Standardize and document workflows to enable speed and scale

Enablement & Advisory
  • Provide ongoing training to Sales on pricing, deal construction, and quoting with a strong focus on the why behind the strategy
  • Contribute to and maintain a self-service Deal Strategy Playbook
What We're Looking For:
  • 5+ years of experience in Deal Desk, Deal Strategy, Commercial Operations, Revenue Operations, Legal Ops, or Sales Operations
  • Proven ownership of complex enterprise SaaS deals from quote to cash
  • Hands-on experience administering or optimizing CPQ tools (Subskribe preferred)
  • Strong Salesforce fluency across quoting, approvals, and deal reporting
  • Solid understanding of enterprise SaaS contracting concepts (order forms, MSA, DPA, SOW)
  • Exceptional communication skills with high emotional intelligence; able to influence without authority
  • Comfortable navigating ambiguity and making judgment calls in fast-paced environments
Nice to Haves:
  • Salesforce Admin experience or certification
  • Legal, contract management, or pricing strategy background
  • Prior sales or customer-facing experience
Why Cresta:
  • Unicorn with backing from Andreessen Horowitz, Sequoia Capital, and Greylock
  • Strong enterprise traction with 20%+ of customers over $1M ARR
  • 2x+ year-over-year growth and record-breaking quarters
  • Opportunity to operate at the center of commercial strategy and enterprise execution
  • Competitive compensation, equity, and comprehensive benefits

Perks & Benefits:
  • We offer Cresta employees a variety of medical, dental, and vision plans, designed to fit you and your family's needs
  • Paid parental leave to support you and your family
  • Monthly Health & Wellness allowance
  • Work from home office stipend to help you succeed in a remote environment
  • Lunch reimbursement for in-office employees
  • PTO: Flexible

Compensation at Cresta:

Cresta's approach to compensation is simple: recognize impact, reward excellence, and invest in our people. We offer competitive, location-based pay that reflects the market and what each individual brings to the table.

The posted base salary range represents what we expect to pay for this role in a given location. Final offers are shaped by factors like experience, skills, education, and geography. In addition to base pay, total compensation includes equity and a comprehensive benefits package for you and your family.

Salary Range: $140,000-$175,000 base + Offers Equity

About Cresta

Cresta is a London-based technology company that specializes in artificial intelligence for the insurance industry. The company was founded in 2017 and provides AI-powered solutions for underwriting, claims, and customer service. Cresta's platform uses machine learning algorithms to analyze data and provide insights to insurers. The company has partnerships with several insurance companies including MetLife and Swiss Re. Cresta has received funding from a number of investors including Greycroft, Deepcore, and Wemind.
Learn more about Cresta
Size
50 employees
Industry
Founded
2017
5 Year Trend
+80%
Revenue
$10 million
NASDAQ

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