Senior Operations Strategy & Enablement Manager

Bestow; United States; Remote; USD 120,000 - 170,000; Full time

Benefits offered by this job

Equity

Remote/WFH options

Dallas office access

Medical/Dental/Vision insurance

Job summary

Bestow is seeking a Sr. Operations Manager to serve as the operational right hand to our leadership, turning intent into execution across dashboards, system changes, and cross-functional initiatives.

You will own reporting, drive capacity planning, and partner with Engineering and Product to unblock dependencies, while applying AI and automation to enhance efficiency and outcomes.

Qualifications

• 5-7 years in operations or execution-focused roles.
• Insurance industry knowledge (life insurance) preferred.
• Demonstrated bias toward action and delivery.

Responsibilities

• Own the reporting layer with dashboards and analyses for leadership decisions.
• Diagnose root causes in efficiency, capacity, and quality; translate into recommendations.
• Collaborate with Engineering and Product to specify requirements and unblock dependencies.
• Configure and deploy system changes with reliable documentation and post-change validation.
• Lead end-to-end improvement initiatives from definition to rollout and measurement.

Skills

Operational leadership

Analytics & reporting

Cross-functional collaboration

Executive communication

Tools

CRM tools

Telephony systems

Workforce management

Tableau/BI tools

RingCentral

Job description

ABOUT BESTOW

Life insurance is one of the world’s most important products. It’s also one of the hardest to build, distribute, and modernize. Bestow exists to change that.

Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation.

Bestow isn’t selling policies. We’re building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise.

Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us.

Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities.

Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov.

ABOUT THE TEAM

Bestow’s TPA Operations Team comprises the Customer Experience (CX), Customer Experience Operations (CXO), and New Business & Underwriting Support (CM) teams and is dedicated to providing outstanding customer experiences through our omni-channel platform. We own the systems, processes, and performance mechanisms that allow Bestow to serve customers and carrier partners at scale, and we are responsible for making that experience faster, smarter, and more efficient. We sit at the center of Product, Engineering and our outsourced partners, translating priorities into working systems and turning day-to-day operational reality into insight the business acts on.

We are a team of 160 people and a high-trust team, which means the work is highly visible and ownership is real.

This role reports directly to the VP of TPA Services, and is open to hybrid in our Dallas office or Remote (US). #LIREMOTE.

WHAT YOU’LL DO

We are seeking a highly organized, technically fluent Sr. Operations Manager to serve as the operational right hand to our operations leadership - the person who turns intent into execution. This role is built for someone who thrives on breadth: one day building the reporting that explains what is happening, the next configuring the systems that change it, the next driving a cross-functional initiative to completion because you were the one who followed up. You will be trusted with high-stakes, ambiguous work where the path forward is not always defined, and judged on velocity, follow-through, and the quality of your thinking.

Key responsibilities include:

Operational Insight & Reporting

• Performance Visibility: Own the reporting layer for the operation — build and maintain the dashboards, trending analyses, and performance reviews that leadership uses to make decisions.

• Diagnostic Analysis: Move past “what happened” to “why,” using data to isolate root causes in efficiency, capacity, quality, and customer outcomes, and translate findings into specific recommendations.

• Capacity & Efficiency: Partner with workforce planning on forecasting, staffing, and productivity analysis; identify and close the gap between planned and realized capacity.

• Systems Ownership & Configuration

• Platform Administration : Serve as a hands-on administrator for our operational and telephony systems — routing, skilling, queue design, IVR and self-service flows, and user configuration.

• Change Execution: Scope, configure, test, and deploy system changes with an eye toward reliability; document what changed and why, and validate impact after the fact.

• Technical Partnership: Work directly with Engineering and Product to unblock dependencies, define requirements in terms they can build against, and represent operational reality in technical decisions.

Process Improvement & Program Execution

• End-to-End Implementation: Own improvement initiatives from problem definition through rollout and measurement — including the unglamorous middle where most initiatives stall.

• Follow-Through Mechanism: Be the accountability layer across partner and planning forums: capture commitments, track them to closure, surface slippage early, and escape with a recommendation rather than a question.

• Roadmap Advocacy: Maintain a clear line of sight into the product and engineering roadmap on behalf of the operation — know what is committed, what has been deprioritized, and what that means for us before it becomes a surprise.

• Enablement & Scaled Delivery: Working with partners and vendors directly to scale tools and operations.

• Frontline Impact: Define success criteria for operational changes and partner with training and quality teams to ensure changes land with the people doing the work.

• Leadership & Influence: Set direction for cross-functional working groups, mentor teammates and analysts, and raise the operational bar without relying on formal authority.

AI & Automation

• Applied AI: Identify where AI and automation can remove manual effort, improve quality, or expand what the team can cover — then build, pilot, and scale it.

• Practical Fluency: Use AI tooling as a daily part of your own workflow to accelerate analysis, documentation, and execution, and help the broader team do the same.

WHO YOU ARE

• We are seeking an operator who moves quickly, closes loops, and is trusted by everyone they work with.

• Experience: 5-7 years in operations, business operations, service delivery, or a similar execution-focused role, with a track record of increasing scope.

• Industry Knowledge: Direct experience in insurance — life insurance, policy administration, underwriting, or carrier/distribution operations. Adjacent fintech or regulated-industry experience with clear insurance exposure will be considered.

• Execution Velocity: A demonstrated bias toward action. You ship, you iterate, and you would rather deliver something useful this week than something perfect next quarter.

• Follow-Through: Nothing you own goes quiet. You track commitments across teams you do not manage and drive them to a decision or a done state.

• Organization: You bring structure to ambiguity — clean documentation, clear owners and dates, and a system for keeping many parallel threads from dropping.

• Analytical Rigor: Comfortable working from raw data to a defensible conclusion, with sound judgment about what the numbers do and do not say.

• Communication: Clear, concise, and audience-aware. You can write the executive summary and run the working session, and you tell people what you need without ambiguity.

• Collaboration: Trusted across functions. You build relationships that let you move faster and are as invested in the partner team’s outcome as your own.

• Leadership: Experience leading initiatives, working groups, or vendor relationships, and mentoring others; formal people management experience is a plus but not required.

Technical Skills:

• Advanced Excel/Google Sheets and working proficiency in SQL for independent analysis.

• Hands-on configuration or administration experience with operational platforms (e.g., CRM, contact center/telephony, ticketing, or workforce management tools).

• Practical experience applying AI/LLM tools to real work, with informed judgment about where they help and where they do not.

• Familiarity with BI tools (e.g., Tableau, Native reporting within phone switch (RingCentral), Salesforce reporting)

• Enough fluency in how software gets built to partner credibly with Engineering and Product.

TOTAL REWARDS

At Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include:

• Competitive salary and equity based on role

• Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs

• 100% paid-premium option for medical, dental, and vision insurance

• Lifestyle stipend to support your physical, emotional, and financial wellbeing

• Flexible work-from-home policy and open to remote

• Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting

• Employee-led diversity, equity, and inclusion initiatives

Recent Employer Awards include:

• Best Place for Working Parents 2023 + 2024 + 2025

• Great Place to Work Certified, 2022 + 2023 + 2024 + 2025

• Built In Best Places to Work, 2022 + 2023 + 2025

• Fortune’s Best Workplaces in Texas 2022 + 2023

• Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024

We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member.

Thanks for considering a job at Bestow!