Trevor Oelschig

Background

Trevor Oelschig is a Managing Director at General Catalyst, which he joined in November 2016 ¹². He holds a BS in Industrial Engineering and Operations Research from UC Berkeley, an MS in Engineering-Economic Systems from Stanford University, and an MBA from the Wharton School ¹³.

Before entering venture capital, Oelschig worked as a Summer Associate at McKinsey & Company in 2006 ². He spent nine years at Bessemer Venture Partners (2007-2016), where he was promoted to Partner in January 2013 alongside Kent Bennett, Brian Feinstein, and Ethan Kurzweil ⁴⁵. At Bessemer, he invested in and served on the boards of several companies that went public, including Shopify (NYSE: SHOP), Instructure (NYSE: INST), 2U (NYSE: TWOU), and PagerDuty (NYSE: PD) ¹³. He also invested in Zapier, Zopa, and Clio during his Bessemer tenure ¹³.

At General Catalyst, Oelschig works with portfolio companies including Aura, Contentful, Fivetran, Grammarly, Housecall Pro, Loom, and Mosaic ¹³. He also led General Catalyst’s investment in Buildkite ⁶.

Stated Thesis

Oelschig has described his investment thesis as focused on individuals: he looks for founders who “live and have an intrinsic understanding of the business they’re building” ¹. He invests in software companies, especially those built by user-focused founders ¹.

His stated interests span “products that bring operational improvements to businesses, big and small, as well as the underlying picks and shovels that help developers build great software and keep systems up and running” ¹.

On the PagerDuty Series B investment, Oelschig stated: “More than ever before, dev and ops teams are having to grapple with keeping their systems and software up and running in a world where these environments are more decentralized, change more frequently, and run at greater scale. PagerDuty has seen incredible traction with customers because it is solving critical revenue-impacting reliability problems that plague every enterprise” ⁷.

On the Buildkite investment, he stated: “It is no surprise to see Buildkite’s phenomenal growth and its distinguished list of customers. Keith is a classic product- and customer-centric builder. The team shares his passion for learning and empowering developers who are building enduring companies across multiple industries” ⁶.

Inferred Thesis

The following analysis is based on 14 verified investments from the portfolio table below. Given that Oelschig has been investing for nearly 20 years across two major firms, this likely represents a subset of his total deal activity.

Sector Distribution (14 verified investments)

• Developer Tools / DevOps: 4 of 14 (29%) — PagerDuty, Zapier, Buildkite, Fivetran
• Enterprise SaaS / Productivity: 4 of 14 (29%) — Grammarly, Contentful, Loom, Mosaic
• E-commerce / SMB Software: 2 of 14 (14%) — Shopify, Housecall Pro
• Education Technology: 2 of 14 (14%) — Instructure, 2U
• Fintech: 1 of 14 (7%) — Zopa
• Legal Tech: 1 of 14 (7%) — Clio
• Cybersecurity: 1 of 14 (7%) — Aura

Note: Aura is categorized separately though it spans multiple categories.

Stage Distribution

At Bessemer, Oelschig invested across stages from seed (Zapier, 2011) through growth rounds. At General Catalyst, his documented investments range from Series A (Buildkite, 2020) to Series C (Housecall Pro, 2018) ². His typical check size at General Catalyst is $1M-$10M with a $6M target ².

Notable Patterns

• Developer and ops infrastructure focus: Nearly 30% of verified investments are in developer tools and operational infrastructure (PagerDuty, Zapier, Buildkite, Fivetran), consistent with his stated interest in “picks and shovels” for developers.
• Multiple IPOs from portfolio: Four of his Bessemer investments — Shopify, Instructure, 2U, and PagerDuty — went public, suggesting strong selection at growth stages ¹.
• Product-centric founder thesis: Across both firms, Oelschig consistently highlights product- and customer-centric founders in his public statements ¹⁶.
• B2B only: No consumer investments appear in the verified portfolio; the focus is exclusively B2B software and services.
• Board-level engagement: He has served on boards at multiple portfolio companies (PagerDuty, Shopify, Instructure, 2U, Clio, Zopa, Zapier, Aura) ¹³.

Portfolio

Note: Years marked with ~ are approximate, based on the period when Oelschig was at the investing firm and when the company raised relevant rounds. Exact investment dates for several companies are not publicly confirmed for Oelschig specifically.

In Their Own Words

“More than ever before, dev and ops teams are having to grapple with keeping their systems and software up and running in a world where these environments are more decentralized, change more frequently, and run at greater scale. PagerDuty has seen incredible traction with customers because it is solving critical revenue-impacting reliability problems that plague every enterprise.” — Trevor Oelschig, PagerDuty Series B announcement, July 2014 ⁷

“It is no surprise to see Buildkite’s phenomenal growth and its distinguished list of customers. Keith is a classic product- and customer-centric builder. The team shares his passion for learning and empowering developers who are building enduring companies across multiple industries.” — Trevor Oelschig, Buildkite Series B announcement ⁶

What Founders Say

No independently sourced founder testimonials found. Oelschig has been described as “a first-call investor who works tirelessly to help his entrepreneurs succeed” in General Catalyst’s announcement of his hire, but this is a firm characterization rather than an independent founder quote ³.

Sources