Associate / Senior Associate

PROOFPOINT CAPITAL

Operator-led Venture Capital firm investing in early-stage Vertical AI

Associate / Senior Associate

Greater Philadelphia, PA | Full-time, in-office

About Proofpoint Capital:

Our objective is to be the best early-stage investor in Vertical AI, and we’re hiring the core team to make this happen. 

Proofpoint is a venture capital firm investing in early-stage Vertical AI with a core focus on Healthcare, Life Sciences, Financial Services, and other regulated, complex industries. Our team founded and scaled category-defining vertical software companies, generating over $40B in enterprise value as Founders and CEOs. The team has also invested together for over a decade, delivering a top-decile track record. These experiences enable Proofpoint to access and win the best opportunities in Vertical AI and deliver superior value creation to the next generation of iconic companies. We are raising a $200M first fund and assembling the core team to help build a top-performing and enduring firm. 

About The Role:

We are hiring an investor to join our team in Philadelphia. We are open to either the Associate or Senior Associate level and will calibrate title and scope to the right person.

This is a full-scope investing role at an exciting new firm. You will work directly with our Principal and General Partners across the entire investment lifecycle — sourcing, diligence, portfolio support, and firm-building — with real ownership from the start. You will be the engine of the deal team, running first-pass screens, owning research and analysis workstreams, building financial models, and drafting the memos that shape our conviction, all using the latest and proprietary AI tools for the investment process. As you ramp, you will generate proprietary deal flow, run diligence processes end to end, and take on more responsibility in supporting the portfolio. Because we are building a new firm, you will also help refine and improve how we work: the systems, the tooling, and the standard for what good looks like.

This is a rare opportunity to join the early team of a new firm. There is significant growth potential, and you will be mentored by seasoned operators and investors along the way.  

Responsibilities:

Drive deal sourcing, network building, and screening

• Develop relationships with founders, operators, co-investors, and accelerators. Represent Proofpoint at conferences, events, and in the communities where Vertical AI founders operate.
• Generate deal flow through proprietary relationships, outbound outreach, and AI sourcing agents.
• Serve as a first point of contact for new opportunities. Run initial screening conversations, populate investment scorecards, and make a clear recommendation on next steps.

Lead due diligence and deal execution 

• Own the analysis on active deals — financial analysis, market sizing, competitive landscape mapping, customer and reference calls, valuation analysis, and technical evaluation.
• Build financial models that enable high-quality decision making (three-statement financial models, unit economics, cap tables, and returns models).
• Author investment memos that succinctly summarize diligence findings and support a point of view.
• Develop investment theses on Vertical AI sub-sectors, and publish briefs that sharpen where we play.

Support our portfolio companies

• Take board observer responsibilities on select companies, including board meeting preparation, note taking, and follow-through between meetings.

Build and strengthen the operations

• Contribute to our technology stack. Build and maintain our proprietary CRM and internal tooling, and evaluate AI tools and data sources to sharpen how we source, diligence, and engage.

Who We're Looking For:

Experience

• 2–8 years of experience in venture capital, growth equity, private equity, or related roles such as banking, consulting, or finance and strategy inside a start-up or large tech company
• Experience in enterprise software/technology is preferred 
• Strong academic and professional track-record

Skills

• Financial analysis and three-statement financial modeling
• Advanced proficiency in Excel, PowerPoint, and other office software
• AI fluency and interest in the latest tools (Claude, ChatGPT, etc.)
• Excellent written and verbal communication; ability to distill complex topics into concise presentations

How you work

• Data-driven and analytical. You think in frameworks and systems – whether it’s analyzing teams, markets, or businesses; you rely on data and logic to drive your decisions.
• Relationship-builder. You can develop genuine relationships with founders, investors, and executives.
• Deeply curious. You have a desire to learn and build expertise in new industries, technologies, and trends.
• Fast learner. You learn rapidly, develop a strong point of view, and communicate it clearly.
• Self-motivated and highly productive. You have a strong work ethic and thrive in a fast-paced environment.
• Confident, humble, and coachable. You have the confidence to develop and communicate your perspectives, but you also listen with an open mind, accept feedback, and seek continuous growth.

Compensation:

Competitive cash and equity compensation. Final title and compensation will reflect experience.