Job Description

About Us

Pearl is AI for professional services at global scale, combining advanced AI with verified human expertise to deliver help that is accurate, accountable, and fast. Since 2003, our network has connected millions of customers with licensed professionals across 196 countries, making real expertise available anytime, anywhere.

Our Values

• Data driven: Data decides, not egos
• Courageous: We take risks and challenge the status quo
• Innovative: We're constantly learning, creating, and adapting
• Lean: We focus on customers, using lean testing to learn how to serve them best
• Humble: Past success is not a guarantee of future success

About the Role

We’re seeking a world-class, market-facing strategist to serve as EVP, Investor Relations & Corporate Development, helping shape the next chapter of Pearl’s journey and fuel a global AI platform that empowers independent professionals to grow, scale, and succeed.

This full-time role is structured as an 18-to-24-month journey, offering the opportunity to lead high-impact work during a key period of strategic growth and operational evolution.

Reporting directly to our CEO, you’ll serve as a business architect and strategic thought partner, shaping company strategy, optimizing our portfolio of brands, and building a compelling blueprint for sustainable, long-term value creation.

This role goes beyond financial discipline. It’s about shaping Pearl’s value story, making the numbers support it, and building confidence with investors, strategic partners, the Board, and other external stakeholders.

You’ll build on an already strong FP&A foundation. This is not an accounting, controllership, or finance reporting role. Your focus will be investor relations, corporate development, strategic finance, long-term value creation, and market-facing leadership alongside the CEO.

You Are:

• A strategic storyteller who sees financials as the language of vision and enterprise value.
• Energized by shaping outcomes, not just reporting them.
• Comfortable engaging directly with investors, analysts, the Board, and strategic partners.
• A proactive, outbound relationship builder who will hustle to expand Pearl’s strategic network and not wait for inbound investor interest.
• A partner to the CEO who thrives in high-velocity, founder-led environments.

You Are Not:

• A traditional CFO, controller, FP&A, or accounting leader focused primarily on budgets, reporting, controls, or month-end discipline.
• Someone primarily motivated by the CFO title or a long-term maintenance role. This is an 18-to-24-month strategic growth journey.

What You’ll Do

• Shape Pearl’s Value Story and Strategic Finance Blueprint: Define and execute a strategy that positions Pearl for long-term value creation, strategic clarity, and compelling external communication.
• Optimize Business Models: Refine our multi-channel strategy (lead generation, B2C, B2B) and develop scalable financial models that highlight future potential and resilience.
• Tell the Strategic Story: Partner with the CEO to communicate our vision and performance with clarity and conviction to investors, the Board, employees, and key external stakeholders.
• Expand Investor and Strategic Networks: Build and nurture relationships with financial, industry, and strategic partners, including investors, analysts, advisors, and ecosystem leaders, to elevate Pearl’s visibility, credibility, and growth opportunities.
• Lead Corporate Development and Strategic Growth: Surface, evaluate, and help execute high-value strategic partnerships, business development opportunities, and growth initiatives that could accelerate enterprise value.
• Unlock Portfolio Value: Evaluate and prioritize growth opportunities across brands, markets, products, and channels to maximize enterprise value.
• Lead a High-Performing Team: Develop and mentor a world-class finance organization focused on insight, impact, execution, corporate development support, and market-facing readiness.
• Drive Strategic Readiness: Ensure financial and operational readiness that supports disciplined planning, scalable growth, and informed decision-making without positioning the role as a traditional CFO search.

What We’re Looking For

• 15+ years of progressive leadership across investor relations, corporate development, strategic finance, investment banking, private equity, top-tier management consulting, or market-facing finance roles; CFO or divisional CFO experience is helpful but not required.
• Proven success shaping company narratives for sophisticated investors, Boards, lenders, analysts, or strategic partners.
• Demonstrated ability to connect financial insight, operating performance, and strategic vision into a persuasive value-creation story.
• Background in corporate development, business development, capital markets, private equity, investment banking, or strategy, with in-house operational exposure strongly preferred.
• Experienced across multi-channel, digital, B2C, B2B, marketplace, or subscription-based business models.
• Strong communicator with boardroom presence, executive gravitas, commercial instincts, and the ability to build confidence externally.
• MBA or advanced degree preferred.

Why You’ll Love It Here

At Pearl, we blend AI innovation and human expertise to make a meaningful global impact. You’ll work directly with a visionary founder and leadership team to shape strategy, scale growth, expand strategic relationships, and define what’s next, all while driving long-term enterprise value in a high-growth environment.

Pay Transparency

Pearl will provide pay transparency information upon application to those in qualifying jurisdictions. ( Employment is with JustAnswer LLC, a Pearl company.)

Our Commitment to an Inclusive Workplace

We welcome people from all backgrounds who seek the opportunity to help build a future where professional services are readily available to all. If you have curiosity, passion, and a collaborative spirit, come work with us. Pearl is committed to an inclusive workplace. Pearl is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, disability, age, or other legally protected status.

AI Disclosure & Informed Consent

Artificial intelligence (AI) technology may be used during the hiring process to record, transcribe, analyze, and rank interview responses. By submitting your application and participating in the interview process, you acknowledge and consent to the use of AI technology in the hiring process. For more information see our AI Disclosure and Consent Policy
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