4 VCs and 4 funds investing in enterprise software
Co-Founder & Partner
First Round Capital
Check: $500K-$3M (seed only)
The seed-stage specialist. Invests earliest and deepest at seed — First Round was one of the firms that pioneered institutional seed investing. Built First Round into a platform that punches well above its check size — extensive founder community (~1000 active founders), expert network (First Round Network), and operational support. First Round Review (their media arm) produces some of the best tactical startup content anywhere — deeply researched guides on hiring, product, management, and go-to-market. Believes the best seed investors win by helping, not just funding. Josh's personal background as a serial entrepreneur (Half.com, Infonautics) gives him deep empathy for founders. He's lived the founding journey and knows what early-stage companies actually need. First Round's community model is a key competitive advantage — founders help each other, creating a network effect that makes the fund more valuable with every new investment. Known for being one of the most founder-friendly VCs — fast to respond, honest about passing, and genuinely helpful when invested.
Co-Founder & Managing Partner
BoxGroup
Check: $500K-$5M (recently raised a $550M fund in Oct 2025, significantly larger than previous funds)
One of the most active and respected seed investors in NYC. Co-founded TechStars NYC (now Techstars NYC), deeply embedded in the New York startup ecosystem since its earliest days. Known for being highly accessible, fast to decide, and genuinely helpful post-investment. Just raised a $550M fund (Oct 2025) — a massive step up from previous funds, signaling BoxGroup's evolution from small seed fund to significant early-stage player. Not thesis-driven — David reacts to founders and ideas he finds compelling rather than fitting investments into a predefined framework. This flexibility has served him well — his portfolio spans fintech (Plaid), healthcare (Oscar, Ro), consumer (Harry's, Away), and more. The common thread isn't sector but founder quality and early product-market fit signals. David is deeply connected to the NYC startup ecosystem and has helped shape it over the past 15+ years. He's often one of the first calls founders make when starting a company in New York.
Partner
Bessemer Venture Partners
Check: $1M-$100M+ (multi-stage, BVP has $3.6B+ under management)
The cloud computing investor. His annual 'State of the Cloud' report is the definitive industry reference for cloud/SaaS metrics. Bessemer's 'Cloud Atlas' benchmarking tool is used by thousands of SaaS companies. The firm publicly lists its 'Anti-Portfolio' — companies they passed on (including Apple, Google, Facebook, Intel) — as a reminder of humility. Data-driven, metrics-obsessed approach to SaaS investing. Has been investing in cloud for over two decades, since before 'cloud' was even a common term. Believes AI will fundamentally transform labor-intensive enterprise processes and that the next generation of cloud companies will be 'AI-native' rather than AI-augmented. BVP created the BVP Nasdaq Emerging Cloud Index (EMCLOUD) tracking public cloud companies — a widely referenced industry benchmark. Byron sees vertical SaaS (purpose-built cloud for specific industries) as one of the largest remaining opportunities.
Co-Founder & Venture Partner
Craft Ventures
Check: $1M-$50M
Pioneered 'Bottom-Up SaaS' — the strategy of applying consumer growth tactics to B2B products. At PayPal he learned viral distribution; at Yammer he proved it could work in the enterprise, growing from zero to $56M ARR in under four years before selling to Microsoft for $1.2B. The core filter is predictable, compounding recurring revenue with strong unit economics. Invented the 'Burn Multiple' metric (net burn / net new ARR) that has become an industry-standard efficiency benchmark. Believes the best SaaS companies combine the growth potential of B2C with the enterprise budgets of B2B. Invested in 20+ unicorns. Operator-investor who thinks in SaaS metrics and has published detailed frameworks (Burn Multiple, Difficulty Ratio, The Cadence, Pipeline Metrics) that founders can reverse-engineer. Recently transitioned from General Partner to Venture Partner at Craft as the firm moved away from seed-stage investing.