Top Senior Level Jobs in Boston, MA

Own the insurance product vision, strategy, roadmap, and full lifecycle for small business customers. Lead agile delivery, business cases, test-and-learn initiatives, regulatory and carrier compliance, competitor analysis, and profitable growth across state portfolios. Partner with technology, marketing, and legal teams, communicate product strategies to stakeholders, mentor junior employees, and improve internal processes using SQL, Looker, and Amplitude insights.

Leads Robin’s Technical Support team, including specialists and a Support Operations Manager. Responsibilities include coaching staff, managing KPIs and ticket queues in Jira, resolving escalated customer issues, improving support processes and documentation, identifying issue trends, partnering with Engineering and Product on root-cause fixes, and adopting AI-assisted support tools.

Leads corporate development for wealth management, sourcing and executing acquisitions, investments, joint ventures, and strategic partnerships. Evaluates strategic fit, market dynamics, financial models, valuations, transaction returns, risks, and growth opportunities. Leads cross-functional diligence, negotiations, approvals, integration planning, and executive or Board communications. Partners with senior leaders across wealth management and corporate functions while developing analysts through coaching, mentoring, recruiting, and training.

Own the direct sales motion for CarGurus data products: prospect and qualify buyers, run consultative enterprise sales, scope data assets and delivery, close deals, and coordinate delivery. Drive dealer monetization, generate customer intelligence, and feed market learnings to Product, Data, and Strategy teams to inform pricing and roadmap.

Own the Toast Delivery Services product roadmap, improving dispatch, order tracking, exception handling, refunds, and AI-assisted delivery operations. Partner with Guest, POS, Order Management, AI teams, restaurants, couriers, and external integration partners to deliver measurable outcomes for operators and guests. Shape real-time delivery experiences, proactive alerts, capacity matching, and trusted automation for restaurant delivery.

Lead Toast’s high-volume customer training team across U.S. and international markets. The role owns training strategy, scalability, quality standards, scheduling, capacity planning, team development, stakeholder alignment, and data-driven program improvement. It also guides AI adoption in live training, content development, and trainer coaching while partnering with Customer Success, Product, Marketing, Learning Design, and Enablement teams to improve customer adoption and retention.

Manage strategic enterprise SaaS accounts, guiding implementation, adoption, value realization, renewals, and expansion. Build relationships with business and IT executives, create customized success plans, monitor customer health, mitigate risks, and deliver business reviews. Partner with Sales, Professional Services, and Solution Integrators to ensure successful deployments and achieve retention and growth targets.

Leads quality, coaching, leadership development, performance improvement, and change management across lottery fulfillment centers. Uses analytics to identify trends, establish KPIs, improve customer experiences, and guide operational decisions. Manages project managers, oversees cross-functional initiatives, supports adoption of new processes and technologies, and ensures compliance with regulatory requirements. The role requires stakeholder influence, team leadership, complex project management, and travel to fulfillment centers nationwide.

Manage DraftKings Rewards loyalty program operations by monitoring KPIs, analyzing player behavior and program economics, validating data, and recommending improvements. Coordinate testing, launches, and issue resolution for program enhancements while partnering with Analytics, Finance, and Loyalty Operations. Build data-backed business cases, improve reporting and workflows through AI and automation, and communicate recommendations to leadership.

Build and manage relationships with VIP players, drive sales and net revenue growth, analyze customer and performance data, identify personalized engagement opportunities, resolve escalations, and follow responsible gaming policies. The role requires strong relationship-building, customer-focused problem solving, revenue strategy knowledge, and the ability to obtain and maintain state gaming licenses.

Administer and optimize Gainsight, Gong, and related Customer Experience systems. Build workflows, health scores, dashboards, integrations, and customer success programs supporting onboarding, renewals, and risk mitigation. Maintain data integrity, gather requirements, lead system enhancement projects, and collaborate with CX, Product, and RevOps teams. Provide training, documentation, stakeholder communication, and operational insights through KPIs and reporting.

Owns infrastructure security across AWS, Azure, and GCP cloud environments. Defines security standards, IAM policies, secrets management, guardrails, and infrastructure-as-code controls. Conducts threat modeling, vulnerability assessments, and penetration testing; monitors alerts and leads incident response. Drives SOC 2 and ISO 27001 compliance, audit readiness, and AI-assisted threat detection. Partners with platform, engineering, operations, legal, and business stakeholders to remediate risks and strengthen cloud security.

Manage complex software contract negotiations and deal structuring while supporting sales teams. Optimize pricing, revenue, profitability, risk, and sales-cycle efficiency within commercial and financial guardrails. Partner with legal, finance, revenue, product, and sales operations teams; oversee deal financials and revenue-recognition implications; support customer-facing negotiations, non-standard deals, policy enforcement, and commercial-process improvements.