Chief of Staff, StealthCo at 25madison

StealthCo is building a fully owned and operated title insurance platform to modernize a legacy industry through purpose-built, proprietary software. By embedding technology directly into acquired companies, StealthCo aims to improve workflow efficiency, standardize operations, enhance visibility across the business, and drive margin expansion over time.

StealthCo is backed by 25madison, a software building and buyout investment platform, with a decade-long track record of developing impactful software for highly regulated, legacy industries. StealthCo aims to be a category-defining disruptor in the real-estate ecosystem by partnering with founders and management teams to help them scale and take their businesses to the next level.

The Role

StealthCo is hiring a Chief of Staff to work directly with the CEO to build the platform from the ground up. As one of the first executive hires, you'll help turn strategy into execution by leading post-acquisition integrations, building scalable processes, establishing operating rhythms, and creating the visibility needed to make fast, informed decisions. You'll work across every part of the business, helping build the operational foundation that allows the platform to scale.

This is an executive role, reporting to the platform's CEO, presenting at Board Meetings and making the case for acquisitions at Investment Committee. We’re looking for someone who can lead and learn with humility.

Responsibilities

• Partner with CEO to define OKRs across the platform, then own the OKR process including setting strategic goals and tracking organization performance.
• Work with Finance team to build and manage key models for the platform and acquired companies.
• Own the post-acquisition integration and execution for each newly acquired business. Nothing is more important than the first 30/90/180 days of our acquired companies, and you’ll be responsible for both the operational and cultural integration.
• Oversee continuous change management through communications and milestones.
• Analyze performance across the platform's subsidiaries, identify operational and financial weaknesses, and develop strategies to improve performance.
• Own key diligence workstreams when evaluating new acquisition opportunities.
• Create collateral content to share with future sellers, investors, co-investors, etc.
• Develop and manage marketing content that strengthens the company’s brand positioning and industry presence across LinkedIn, Facebook, and other digital channels.

What We're Looking For

• You are a flexible executive who can navigate ambiguous, unstructured environments and can build processes from scratch.
• You are a prompt and clear communicator with strong interpersonal and leadership skills.
• You are a fast learner. You likely won’t have experience across each business line, so you are an analytical thinker who can quickly understand new businesses, identify key performance drivers, and evaluate opportunities for margin improvement.
• You can demonstrate measurable skills across financial modeling and analysis. This is a math-heavy role, and you have to be comfortable working from and building models.
• You are up to date on modern AI and technological tools. There are cheat codes, and you maintain knowledge and mastery of tools and processes.
• You understand business and profit. We love technology and company building, and we use those tools to generate revenue and profit for our companies. You understand the various levers to pull to maximize business outcome.
• You are a curious person who loves to learn and take on new challenges. This is a hard job with awesome opportunity, and you relish the chance to lean in.
• You have experience in FinTech, consulting, real estate or investment banking.

Experience: 5-8 years of experience in management consulting, investment banking, financial due diligence, software start-ups, or similar roles. (Experience in real estate and real estate tech is a plus).

Education: Bachelor’s Degree required. MBA, MSF, or JD preferred. You have experience quickly mastering new concepts, and you have the academic record to back it up.