Strategy and Planning Lead

About You

You are a highly strategic, exceptionally organized, and proactive leader who thrives in a fast-paced, entrepreneurial environment. You anticipate needs, identify opportunities, and drive initiatives forward with minimal guidance. You bring clarity to ambiguity and do not wait to be told what to do. You are an expert at synthesizing complex information for executive consumption and know how to prioritize what truly warrants the CEO's attention. Conversely, you can serve as the CEO's proxy, ensuring key messages and priorities are communicated clearly and concisely across the organization.

You are an exceptional communicator, a constant learner, and have a strong desire to learn how fintech startups define strategy, operate, and scale. You build strong relationships across teams and know how to influence without formal authority. You are not afraid to roll up your sleeves and tackle diverse challenges, from high-level strategic planning to detailed operational execution. You have a strong bias towards action and possess a default positive attitude, a collaborative approach, outstanding character, and grit.

About the Role

As Strategy and Planning Lead, you will serve as a critical strategic partner and operational extension of the CEO, playing a pivotal role in driving Flourish's growth and operational excellence. This is a unique opportunity for an ambitious professional to gain broad exposure across all facets of a rapidly scaling WealthTech company.

The Strategy and Planning Lead will play a key role in executive tasks such as maintaining a strong relationship with MassMutual, Board preparation, leadership updates, financial forecasting and modeling, and driving execution. Additionally, you’ll serve as an extension of the CEO and Flourish’s Operating Committee, providing support for and oversight of the highest priority company-wide initiatives, from strategy to execution.

The role requires strong cross-functional collaboration, particularly across the Flourish Operating Committee, General Counsel, and others in leadership. You will often serve as a proxy for the CEO to ensure strategic initiatives are being consistently prioritized and key messages are reinforced throughout the organization. The Chief of Staff will be a trusted sounding board and confidant for the CEO and other key leaders within Flourish and will act as a force multiplier across the organization.

Principal Responsibilities

• Act as a strategic thought partner and proxy for the CEO across the organization, attending key meetings, representing the CEO's perspective, and ensuring alignment across leadership teams
• Partner closely with Flourish's Operating Committee to translate high-level business strategies into concrete operational plans in pursuit of a culture of execution and excellence
• Develop relationships with key leaders in the organization to synthesize key information to the CEO and identify areas in the organization that require the CEO's attention
• Lead, navigate, and facilitate collaboration between departments across product, engineering, sales, marketing, operations, legal, and more, ensuring departmental goals align with overall company objectives
• Organize and manage key organizational processes, such as monthly company meetings, OKR development and tracking, financial forecasting and budgeting, hiring plans, and strategic offsites
• Lead and manage critical cross-functional projects and initiatives, ensuring timely execution, resource allocation, and clear accountability
• Conduct financial modeling and analysis for key strategic projects, potential partnerships, and new business initiatives, providing data-driven insights to support executive decision-making. Collaborate with Flourish’s Operating Committee to evaluate market trends, advisor and customer needs, and competitive positioning to drive growth initiatives
• Develop and manage internal communication across the organization, including preparing presentations, reports, memos for board meetings, and other stakeholder updates
• Proactively identify operational bottlenecks, strategic challenges, and areas for improvement, proposing and implementing effective solutions
• Nimbly manage multiple priorities and projects to help the CEO drive delivery and execution of the company strategy

Minimum Qualifications

• Bachelor's Degree or relevant experience
• 5+ years of experience in a fast-paced, high-growth environment, preferably within financial services, fintech, or technology
• Proven ability to manage complex projects and drive cross-functional initiatives
• Strong analytical and quantitative skills, with experience in financial modeling and data analysis
• Strong presentation and deck building skills
• Exceptional written and verbal communication skills, capable of interacting effectively with all levels of an organization
• Demonstrated ability to operate with a high degree of autonomy and discretion
• Due to the nature of this position, as part of the background check process, candidates must be able to pass a fingerprint background check to qualify as a fingerprinted person under FINRA. For roles requiring registration, additional regulatory screenings may apply, including a review of Form U5 disclosures and other relevant licensing information.

Preferred Qualifications

• Degree in a relevant field (e.g., Finance, Business Administration)
• Experience in a Chief of Staff, Head of Operations, or similar strategic/operational leadership role
• Prior experience in the WealthTech or RIA industry
• Prior startup experience

At Flourish, we focus on ensuring fair, equitable pay by providing competitive salaries, along with bonus and incentive opportunities and benefits for all employees.

Base Salary Range: $128,000 - $168,000 plus bonus

Disclosures:

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status.