AI Savvy Director, Strategic Programs - Office of the CEO

About Us

Expedite Commerce is a Salesforce-native Lead-to-Cash SaaS platform offering advanced Digital Engagement, Configure, Price Quote (CPQ), Contract Lifecycle Management (CLM), eCommerce, and Subscription Billing. We are accelerating growth through an AI-first approach, improving both customer experience and operational productivity.

Re:them is an AI-driven software company revolutionizing the sales process by empowering buyers to make informed decisions. Our platform uses AI to guide insightful questioning, uncovering customers' needs, and the impact of potential changes. We’re reshaping not only direct sales but also enhancing customer service.

We plan to spin up additional companies over time, each with its own unique impact on the technology landscape. This role offers the opportunity to be a part of multiple ventures, each poised for significant growth and success.

Role Overview

We are seeking a strategic, AI-savvy operator to join as Director, Strategic Programs – Office of the CEO. This high-impact role blends program leadership, CEO enablement, investor engagement, and cross-functional execution.

This individual will serve as a rotational initiative leader, stepping in to launch and scale critical business functions during their formative stage, before those functions are transitioned to permanent leadership. The first program in scope is the development and activation of Expedite Commerce’s Indirect Channel Program—a vital new go-to-market motion.

You will also work closely with the CEO and Executive Leadership Team (ELT) to track and report on company-wide milestones, KPIs, and strategic alignment, helping ensure operational clarity and accountability at scale.

Key Responsibilities

CEO Strategic Execution

• Keep leadership accountable to strategic Initiatives and milestones to ensure velocity
• Manage dashboards to report on company-wide KPIs, and help ensure cross-functional alignment
• Synthesize insights and risks into executive updates and action plans

Strategic Program Leadership (Interim Ownership Model)

• Fill leadership gaps across emerging initiatives and business functions until long-term ownership is established
• Example: serve as interim lead for launching Expedite Commerce’s Indirect Channel Program— working with CMO and CEO on refining strategy, onboarding partners, and driving early traction
• Build repeatable playbooks, metrics, and transition plans for each program

AI Transformation Leadership

• Co-lead the company’s AI Task Force, translating the CEO’s AI-native vision into tactical, high-impact projects
• Identify workflows ripe for automation or augmentation, and implement pilots with functional leaders
• Champion a culture of AI-first thinking and continuous improvement

Investor & Messaging Support

• Collaborate on and polish pitch decks, investor updates, and due diligence materials
• Hold initial meetings with interested investors, articulate company vision, and collect feedback for the CEO
• Work with finance partners to ensure financial narratives are crisp and data-backed

CEO Brand & Visibility Enablement

• Support CEO’s external presence: book promotions, podcast outreach, speaking engagements
• Help orchestrate repeatable systems for content creation, and brand consistency
• Act as a messaging partner to amplify the CEO’s presence across ventures and channels

Bonus Personality Note

If you read this far and thought, “This sounds like a modern-day Donna from Suits — but with AI superpowers and a startup edge,” you're exactly who we’re looking for.

We’re seeking someone who can anticipate, execute, and elevate — not just follow instructions. Someone who can be in the room where it happens, help make it happen, and then turn it into a playbook for scale.

Ideal Candidate

• 5–8+ years of experience in high-growth SaaS, consulting, or operational leadership roles
• Strategic operator who thrives in ambiguity and takes full ownership of execution
• Strong communicator with executive presence and a sharp eye for details
• Experienced or highly curious about leveraging AI to drive transformation
• Passionate about scaling businesses, building systems, and doing high-leverage work

Why Join Us?

• Strategic Impact: Work directly with the CEO to drive initiatives that shape the future of multiple companies.
• Cross-Venture Exposure: Gain experience across Expedite Commerce, Re:them, and future ventures.
• AI-Driven Environment: Join a team committed to becoming AI-native, where innovation isn’t optional — it’s the standard.
• Dynamic Growth: Be part of a company scaling from 10 to 100, with a chance to rotate into bigger leadership roles.
• Visibility & Trust: Step into a high-autonomy, high-influence role with full executive visibility.

Location

Remote-first with occasional travel for strategy sessions, off-sites, or investor meetings.

• Health Insurance
• Company-paid, accredited professional certifications aligned with your role
• Fully remote work opportunity with flexible scheduling
• Direct exposure to strategic initiatives across multiple high-growth ventures
• Opportunity to rotate through company-building leadership roles
• Close collaboration with the CEO and Executive Leadership Team
• Immersive experience in building an AI-first organization

About Expedite Commerce

At Expedite Commerce, we believe people achieve their best when empowered by technology that removes friction, sparks curiosity, and accelerates action. Our Salesforce-native Lead-to-Cash platform helps B2B companies configure, price, quote, sell, bill, and scale — all with unmatched accuracy and speed.

Our sister company, Re:them, is reshaping the sales journey by enabling buyers to self-discover the value of change through AI-driven questioning and insight. Together, we’re building a portfolio of ventures built around one core principle: designing the future of work with AI at its core.

We’re not just digitizing processes — we’re building companies of the future, and this role will put you right at the heart of that mission.

See more about us at expeditecommerce.com.
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