Sr. Deal Strategy & Operations Specialist - remote

Jobgether•Colorado Springs, CO

2d•Remote

About The Position

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior Deal Strategy & Operations Manager - REMOTE. In this critical role, you will act as a strategic partner directly impacting the commercial strategy and operations. You will be responsible for managing complex enterprise deals, collaborating with various teams, and driving process improvements that enhance efficiency and revenue. This role emphasizes the importance of executing high-value transactions while ensuring compliance with company standards. Join us in this exciting opportunity to shape the future of the workforce with AI-driven strategies.

Requirements

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

Responsibilities

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
Drive end-to-end improvements across the quote-to-cash lifecycle
Define business requirements and partner with systems teams on enhancements for deal tools
Lead UAT and rollout of new deal processes and tooling
Provide ongoing training to Sales on pricing, deal construction, and quoting

Benefits

Unicorn with backing from top-tier investors such as Andreessen Horowitz and Sequoia Capital
Strong enterprise traction with 20%+ of customers generating over $1M ARR
2x+ year-over-year growth and record-breaking quarters
Opportunity to contribute to commercial strategy and enterprise execution
Competitive compensation, equity, and comprehensive benefits
Variety of medical, dental, and vision plans to fit employee needs
Paid parental leave to support employees and their families
Monthly Health & Wellness allowance
Work from home office stipend
Flexible PTO policy