Senior Business Operations and AI Associate

Bestow is a leading insurance technology platform serving some of the world's largest and most innovative life insurers. We are on a mission to increase financial stability for everyone. Bestow is a team of mission-driven, results-oriented individuals. We offer all employees a remote (contiguous 48 only)/hybrid workplace, meaningful benefits, substantial growth opportunities, and equity.

Bestow participates in the E-Verify Program.

The Business Operations Team at Bestow serves as the strategic engine guiding operational excellence and transformational initiatives across the company. This team is a key part of executive leadership, working closely with the founders as a high-impact team that operates at the intersection of strategy and execution. We lead the company's most critical cross-functional initiatives, including spearheading transformative AI work, establishing and communicating our corporate strategy, overseeing operational initiatives across various functions, and leading corporate development efforts.

This role is a hybrid role based in Dallas, Texas.

We are seeking a versatile and driven Associate who brings both strategic consulting rigor and startup execution velocity to drive operational excellence and champion AI adoption across our organization. This position is ideal for someone who has honed their analytical and strategic thinking skills at a top-tier consulting firm and has subsequently demonstrated their ability to execute in a fast-paced startup environment. This role reports to the Head of Business Operations and works closely with our executive team; it is highly impactful and visible, with clear opportunities to drive demonstrable impact for Bestow. Your job will span Core Business Operations, and your first major initiative is leading Bestow’s cross-functional AI initiatives. Key responsibilities include:

• Strategic Initiative Leadership: Own end-to-end execution of strategic initiatives from problem definition through implementation, managing stakeholder alignment, and driving measurable business outcomes.

• Process Transformation: Lead complex, cross-functional process redesigns while ensuring functional implementation in our startup environment.

• Advanced Analytics & Insights: Build sophisticated financial models, conduct deep-dive analyses, and create executive-ready presentations that drive C-suite decision making.

• Business Case Development: Create comprehensive business cases for new initiatives, including financial modeling, risk assessment, and implementation roadmaps.

• Operational Cadence: Establish and run critical business rhythms, including OKR planning, executive business reviews, and cross-functional steering committees.

• Executive, Board & Investor Relations: Own preparation of executive leadership decks, board decks, investor updates, and strategic analyses; support data rooms for fundraising and M&A activities.

• AI Strategy Development: Partner with executive leadership to execute our enterprise AI strategy, including capability roadmap, investment priorities, and competitive positioning.

• Program Management: Own the AI Champions program end-to-end, recruiting champions, facilitating monthly sessions, tracking departmental progress, and scaling successful use cases company-wide.

• Complex Implementation Leadership: Lead AI transformation projects that span multiple departments, drive effective AI adoption across functions, with varying technical complexity, and ensure sustainable adoption.

• ROI & Business Impact: Establish measurement frameworks that quantify AI impact on revenue growth, cost reduction, and operational efficiency.

• AI Technology Selection Strategy: Lead vendor evaluations, manage proof-of-concept testing, and implementation across teams.

• Knowledge Management: Design and deliver AI workshops, create certification pathways, and build a scalable knowledge management system for AI best practices.

• Risk & Governance: Partner with Compliance and Legal to reinforce enterprise AI policies, conduct risk assessments, and ensure compliance with emerging AI regulations.

We are seeking an individual who excels in a fast-paced environment and is passionate about the future of AI in operations.

• Education: Bachelor's degree required; MBA or advanced degree is not required.

• Consulting Foundation: 2+ years at a leading management consulting firm (McKinsey, Bain, BCG, Deloitte, etc.) with experience across multiple industries and functional areas.

• Startup Experience: 1-2+ years in a high-growth startup environment where you've translated strategy into execution and demonstrated an ability to manage complex, multi-stakeholder projects.

• Strategic Thinking & Communications: Ability to structure ambiguous problems, develop hypotheses, conduct analyses, and synthesize complex ideas into simple, comprehensible communications.

• Leadership Without Authority: Proven ability to influence and align cross-functional teams, drive consensus, and navigate organizational dynamics without formal authority.

• AI Leadership: Proven track record of driving AI/automation initiatives with measurable business impact; deep familiarity with the current AI ecosystem and emerging capabilities.

• Technical Excellence:

  • Expert-level proficiency in Excel modeling, SQL, and BI Tools (e.g., Looker, Tableau) for data analysis.

  • Hands-on experience with Generative AI platforms, LLMs, and APIs.

  • Experience with organizational transformation frameworks, building toolkits, and process maps to standardize rollout of new systems or AI programs.

  • Familiarity with software development lifecycle and agile methodologies.

  • Experience with no-code/low-code automation platforms (n8n, Zapier, Make, Retool)

  • Experience moving established prototypes toward enterprise-grade solutions.

• Industry Knowledge: Understanding of insurance, fintech, or B2B SaaS business models; experience with policy administration, underwriting, or actuarial concepts is highly valued.

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

We're proud to be recognized as a top employer, consistently earning accolades for our exceptional workplace culture and commitment to our employees.

• We've been recognized year after year by Great Place to Work, Built In Best Places to Work, and Fortune's Best Workplaces in Texas (2022-2025).

• We've been named one of Fortune’s Best Workplaces in Financial Services and Insurance (2022-2024), a CNBC and Statista World's Top Insurtech Company (2024), and one of The Financial Technology Report's Top Insurtech Companies (2024-2025).

• We're honored to be recognized as a Best Place for Working Parents for three consecutive years (2023-2025).

We value diversity at Bestow. The company will recruit, hire, 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 career at Bestow!

Compensation Range: $150K - $170K