Sienna Blake

Chief Operating Officer

Boston, MA, United States

Professional Summary

Chief Operating Officer with 15+ years of experience scaling SaaS, fintech, and marketplace businesses through disciplined operating systems, customer-led growth, and high-performing teams. Sienna has led multi-region expansions, post-merger integrations, and margin improvement programs that lifted recurring revenue, delivery quality, and employee engagement. She partners closely with boards and executive teams to translate strategy into measurable roadmaps, resilient processes, and accountable execution. Known for calm change leadership, rigorous metrics, and building inclusive cultures that compound results.

Employment History

Chief Operating Officer

Northstar Cloud Systems · Boston, MA

Jan, 2021 · Present

• Scaled operating model from 120 to 420 employees across three regions, increasing on-time delivery from 82% to 97% while sustaining 35% annual recurring-revenue growth. • Built quarterly planning, KPI, and customer-health cadences that reduced executive decision cycles by 40% and improved renewal visibility. • Led integration of a $48M fintech acquisition, consolidating systems and vendors to unlock $6.2M in annualized savings within 12 months. • Established manager coaching and succession programs that lifted engagement 18 points and cut regrettable attrition by 31%.

Vice President, Operations

Harborline Payments · Cambridge, MA

Jun, 2017 · Aug, 2020

• Directed global operations for a 300-person payments platform, standardizing service delivery across North America and Europe and improving gross margin 11 points. Introduced risk, compliance, and incident-response operating rhythms that cut critical incidents 45% and reduced audit preparation time by 60%. • Negotiated strategic vendor portfolio and redesigned onboarding workflows, saving $3.8M annually while reducing time to value for enterprise customers by 28%. Mentored six functional leaders and built a durable operating cadence adopted company-wide after a successful Series C scale-up.

Director of Operations

Cedarline Retail Group · Boston, MA

Aug, 2014 · May, 2017

Directed regional store operations across 28 locations, improving same-store productivity 19% through standardized labor and inventory playbooks Opened 12 new locations on schedule, coordinating leases, vendor readiness, hiring, and manager traini Reduced fulfillment and shrink costs by 14% by redesigning replenishment controls and frontline metrics.ng..

Education

MBA, Operations & Strategy

Northeastern University · Boston, MA

Sep, 2014 · May, 2017

B.S. Industrial Engineering

University of Oregon · Cambridge, MA

Sep, 2012 · May, 2014

Skills

Ability to Multitask

Analytical Thinking Skills

Interpersonal Communication Skills

Customer Relations

Ability to Learn Quickly