Open to opportunities

Caryn Asklar

@carynasklar

Message

Sales Operations & Revenue Operations executive driving scalable systems and forecasting accuracy.

United States

Message

What I'm looking for

I seek leadership roles where I can own CRM/product ecosystems, drive GTM scalability, improve forecasting accuracy, and lead cross-functional operational transformation.

I am a Sales Operations and Revenue Operations executive with 15+ years building operational backbones for high-growth, complex organizations, specializing in Salesforce ownership, sales forecasting, GTM planning, and cross-functional alignment. I translate growth strategy into scalable systems, disciplined execution, and measurable improvements in sales productivity, forecasting accuracy, and operational efficiency.

As an executive product owner of CRM ecosystems, I led multi-year migrations to modern platforms, standardized implementation processes to 99.98% quality, and delivered enterprise dashboards that improved pipeline transparency and decision making. I have led PMO and portfolio governance models, supported large federal and commercial capture efforts, and driven end-to-end operational efficiencies across Sales, Marketing, SDR, Solutions Engineering, and Partner teams.

Experience

Work history, roles, and key accomplishments

Director, Enterprise Sales Operations

EmblemHealth / ConnectiCare

Jan 2018 - Jan 2025 (7 years)

Executive owner of enterprise Sales Operations and Salesforce ecosystem, led multi-year CRM migration and platform optimization that improved sales productivity and forecasting accuracy and standardized implementation processes to 99.98% quality.

Salesforce Sales Operations Sales Forecasting GTM Planning Pipeline Management Data Reporting

Director, Strategic Portfolio & Relationship Management

UnitedHealth Group

Jan 2017 - Jan 2018 (1 year)

Designed and launched enterprise PMO and portfolio governance supporting large-scale GTM and capture initiatives, partnered on major federal and commercial captures including a $65B opportunity, and led platform modernization and operational transformation.

Program Management Capture Management Stakeholder Engagement Regulatory Compliance GTM Strategy Change Management

Senior Program & Capture Leader

UnitedHealth Group

Jan 2013 - Jan 2017 (4 years)

Led federal and commercial capture efforts and translated regulatory and operational requirements into executable solutions, supporting pre-sale planning and executive client engagements for large-scale opportunities.

Capture Management Stakeholder Management Regulatory Proposal Strategy

Director of Account Management

UnitedHealth Group

Jan 2012 - Jan 2013 (1 year)

Directed account management functions, consolidating operations and enabling scalable regional models to improve efficiency and readiness for acquisitions and platform modernization.

Account Management Client Engagement Process Improvement Operational Readiness Vendor Management