Chief of Staff

We're transforming the trillion-dollar world of in-person sales by capturing and analyzing a never-before-digitized dataset: face-to-face conversations. While the tech world obsesses over digital interactions, most of our economy still runs on millions of in-person sales and service conversations happening daily across the U.S. Unlike Zoom calls, these conversations weren't historically recorded – leaving petabytes of rich data untapped. Until now.

Companies in hundreds of industries rely on frontline salesforces working in-person, yet they've operated with zero visibility into these critical customer interactions. Meanwhile, sales productivity follows a stark Pareto distribution – the vast majority of commissions accumulate to a small percentage of top performers, leaving millions of salespeople struggling to achieve financial freedom.

With Siro, we're democratizing sales excellence. Our customers see their reps closing up to 40% more deals, all while gaining unprecedented insights from field conversations.

We've built an intelligence platform that captures, processes, and derives actionable insights from in-person sales and service conversations. Our customers span diverse industries – home improvement, home services (HVAC, plumbing), retail, B2B distribution, insurance, hospitality, and more.

With over $75M in backing from world-class investors, we're on a mission to make field sales the most accessible path to financial freedom.

Our product is already making waves - 4.8 stars on the App Store (700+ ratings), 5.0 stars on G2 (25 reviews), and partnerships with industry leaders like ServiceTitan (NASDAQ: TTAN).

Key Responsibilities

We are seeking a Chief of Staff to act as a true force-multiplier for the CEO. This role is about leverage, decision-making, and execution at the highest levels of the business:

• CEO Proxy — Step in for Jake in high-velocity decisions and meetings, ensuring the CEO’s perspective is represented when he can’t be in the room.

• Strategic Execution — Drive and unblock critical cross-functional initiatives that lack a clear owner (examples: rolling out a new billing structure, structuring a partnership with a strategic player).

• CEO Partnership — Keep the CEO operating at maximum leverage. Provide daily briefings, prep and debrief key meetings, and ensure he has the right context at the right time.

• Board & Investor Relations — Prepare for and coordinate board meetings, handle investor communications, and maximize the value we get from our investor network.

This is not the EA-adjacent version of Chief of Staff. It is a strategic operator role with direct impact across the company.

Requirements

• Exceptional communication skills — written, verbal, and visual (Google Slides, board decks, narratives)

• Analytical rigor — advanced Excel skills and comfort digging into ambiguous, messy data.

• Strong interpersonal skills — able to influence, align, and resolve conflict across teams.

• Low ego, highly collaborative.

• 5-10 Years of Experience. Preferences:

  • Prior Chief of Staff experience

  • 1–2 years at McKinsey, Bain, or BCG

  • Operator experience at a high-growth Series A–D startup (ops, sales, or strategy)

  • Former founder

Why join Siro as a Chief of Staff?

• Direct access to work alongside the CEO on the most important challenges in the business.

• A front-row seat to scaling a category-defining Series B startup.

• A role that spans strategy, execution, and influence across every function of the company.

• The steepest learning curve you can find — this is a dynamic, high-leverage operator role.

Compensation & Details

• Must be open to frequent travel

• Willing to work in-person 5 days per week at our NYC office (Flatiron)

• Compensation (3 levels encompassed): $143k - 220k

At Siro, we are committed to creating a diverse and inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We provide equal employment opportunities to all applicants without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.