Position Summary:

The Chief of Staff at Trulioo is a critical leadership role that drives strategic alignment, operational execution, and organizational effectiveness at the highest levels of the company. Acting as a trusted advisor and right-hand to the CEO, you will ensure that executive priorities are translated into action, internal processes are optimized, and cross-functional collaboration is seamless.

You will work closely with the CEO and the executive team, serving as a thought partner, problem-solver, and operational lead across a wide array of strategic initiatives. This role requires exceptional judgment, discretion, communication, and project management capabilities. The ideal candidate brings a blend of strategic thinking, execution excellence, and operational rigor, paired with the humility and flexibility to operate both behind the scenes and in leadership settings.

A defining part of this role is AI fluency: you will be the executive team's go-to person for identifying where AI tools can remove friction, accelerate decisions, and free up leadership time and you'll model that adoption yourself before asking others to follow.

This is a full-time position available on either a permanent or fixed-term basis, with a preference for a permanent hire. Remote work may be considered for the right candidate

What You'll Be Doing:

• Set and sustain the operating rhythm. Own executive meetings, business reviews, board meetings, and offsites, including agendas, pre-reads, decisions, and follow-through. Ensure everyone leaves clear on what was decided and who owns it.
• Run the goal-setting system. Own the OKR process end-to-end, and give the CEO and leadership team an honest read on where the business actually stands.
• Prepare the CEO for high-stakes moments. Build board materials, executive presentations, and briefings for critical internal and external meetings.
• Lead what nobody owns. Find the gaps, lead the cross-functional initiatives that fill them, then hand them off cleanly. Expect two or three running at a time, including initiatives to identify, pilot, and roll out AI tools that streamline internal processes across teams.
• Extend the CEO's reach. Shape communications for town halls, company updates, and speaking engagements. Stand in for the CEO where appropriate, knowing what to decide and what to bring back.
• Be a candid thought partner. Help the CEO prioritize and pressure-test decisions.
• Champion AI adoption across the executive team. Act as the internal evangelist and coach for practical AI use, identifying high-value use cases, vetting new tools, running lightweight trainings, and helping executives build AI-augmented habits into their own workflows.

What You'll Bring:

• 5+ years of experience in executive operations, management consulting, corporate strategy, project management, or business operations, preferably within a fast-paced tech or SaaS environment.
• Proven experience supporting C-level executives or founders in a Chief of Staff, Business Manager, or Strategic Advisor role.
• Strong strategic thinking and problem-solving capabilities, with the ability to connect the dots and drive clarity across complexity.
• Exceptional written and verbal communication skills, with the ability to craft high-impact executive communications.
• Highly organized, detail-oriented, and able to manage multiple initiatives simultaneously under tight deadlines.
• High EQ and interpersonal intelligence - able to influence, mediate, and build trust across all levels of the organization.
• Absolute discretion and professionalism in handling sensitive and confidential information.