Redpoint

About Us

Logistics is broken. Let’s fix it.

We are a team of engineers, product designers, and customer champions applying the most transformative technology of our times, AI, to one of the largest industries in the world: logistics. Our mission is to streamline freight brokerage, carrier management, and 3PL operations through automation, freeing teams to focus on high-value strategic work.

Overview

As Chief of Staff, you will be the CEO’s thought-partner, operational amplifier, and organizational integrator. You’ll build concrete plans, drive cross-functional initiatives, eliminate operational bottlenecks, and ensure the company stays aligned and focused on high-impact work. This is a highly strategic, high-trust role that shapes the company’s operating rhythm and ensures Augment executes with clarity and velocity.

What You’ll Do

Planning & Execution

• Collaborate with the CEO to define company-wide priorities (OKRs, quarterly goals, long-term roadmap) and translate them into actionable plans.

• Lead or support high-priority cross-functional initiatives, including new business line launches, strategic evaluations, and market or partnership assessments.

• Monitor progress against strategic goals; track key metrics; surface blockers; and drive follow-through and accountability across teams.

Operational Cadence & Organizational Rhythm

• Establish and run the operating rhythms: leadership syncs, company-wide all-hands, quarterly business reviews, OKR tracking, and project status reviews.

• Prepare meeting agendas, pre-reads, and follow-ups; ensure clarity of decisions and alignment after major meetings.

• Build or refine internal processes, workflows, and documentation practices as the company scales across product/engineering, operations, and go-to-market functions.

Cross-Functional Alignment & Communication

• Act as a liaison between the CEO, leadership team, and all functional groups, surfacing interdependencies, risks, and opportunities.

• Ensure teams have clear priorities, strong communication pathways, and minimal operational friction as Augment grows.

Executive Enablement & Decision Support

• Provide analytical and strategic support: gather data, run analyses, and prepare briefs for decisions related to GTM strategy, partnerships, hiring, and product expansion.

• Manage and protect the CEO’s strategic time by filtering priorities, assessing impact, and ensuring focus on high-ROI initiatives.

• Support culture-building efforts, leadership offsites, and internal communications to reinforce clarity, cohesion, and values at scale.

• Optionally support early-stage hiring, recruiting, or people operations for critical roles as the company grows.

• Contribute to external-facing initiatives including strategic partnerships, investor updates (as relevant), and board-level materials.

What We’re Looking For

• Experience in Chief of Staff, strategy, operations, consulting, investment, or similar high-analytical, cross-functional roles.

• Exceptional project management and prioritization skills — you can juggle multiple high-stakes initiatives without dropping details.

• Strong communication and synthesis abilities: you turn ambiguity into structured, actionable plans.

• High EQ and relationship-building skills; you can work fluidly across teams and levels.

• A bias toward action — you notice gaps, propose solutions, and move quickly to unblock the CEO and the company.

• Comfort operating in fast-paced, zero-to-one environments where processes are still being built.

Bonus Points For

• Experience in a high-growth startup, especially in operational, strategic, or executive support roles.

• Exposure to SaaS, AI, logistics, or other complex operational industries.

• Familiarity with OKR frameworks, operating models, or organizational design.

• Experience supporting fundraising, investor communications, or board materials.

Why Join Us?

• Competitive Salary + Stock Options

• Comprehensive Health, Vision, and Dental Benefits

• Flexible PTO

• On-site Gym

• Monthly stipend

About Augment

At Augment, we set out to create a fully autonomous AI platform that streamlines operations and reclaims the human element in logistics. Our founders recognized a pattern: talented professionals were stuck handling manual data entry, phone calls, and repetitive tasks, instead of focusing on high-impact problem-solving and strategic decision-making.

That insight became our mission—to free logistics professionals from busywork so they can focus on what truly drives business growth. Augment isn’t just about efficiency; it’s about transforming an entire industry by empowering teams with AI-driven solutions that make logistics smarter, faster, and more adaptive.

Join us on this journey!

Augment is an Equal Opportunity Employer and values diversity at our company. We consider all qualified applicants without regard to race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, disability, or any other legally protected status.

Augment complies with federal, state, and local laws regarding equal employment opportunity and reasonable accommodation. If you need assistance or an accommodation during the application or interview process, please contact your recruiter.

We also consider qualified applicants with arrest and conviction records in accordance with applicable federal, state and local fair-chance / ban-the-box laws (for example, but not limited to, the California Fair Chance Act).