Sergio Monsalve

Founding Partner

2021

Roble Ventures is a future-of-work focused fund investing $200k-$2M in early-stage technologies that enable people, teams, and organizations to achieve their most ambitious work. Our team has multiple exited unicorns and decades of experience in this space. By combining deep sector expertise with the tenacity of our uncommon founders, we’ll take you as far as you’re willing to go.

Board Member & Investor

2014 - 2021

Partner

2007 - 2020

Investor and board member in 3 multi-$B companies. Source companies and conduct due diligence to determine viability of potential investments. Meet with the CEOs and founders of potential investments. Negotiate term sheets and engage in all aspects of deal closing. I contribute to business and organizational development efforts. Sit on boards and subcommittees and contribute to the people management aspect of invested companies (executive replacement, team re-architecture, Board governance, fiduciary responsibilities, follow-on financing strategy, exit strategy, and execution as M&A and IPO). - Achieved over $500M in total realized and unrealized cumulative net gains during tenure. This results in top quartile venture returns, and includes substantial cash-on-cash realized gains. Over 3x return multiple and a 10-year NET IRR of 22% per year. - Led investment and is board member of Udemy early and it is now valued at over $3B privately; this represents over 7x gain on initial investment. Company has grown 30x in annual revenues since first investment). Outdistanced 4 top-tier firms in winning deal. Played key role in championing the launch of Udemy for Business, a business now privately valued as "unicorn" in just 3 years since launch. - Led investment and was board members of Adaptive Insights that returned 7x cash-on-cash. Assisted with bringing in new leadership. Engaged in extensive due diligence and subsequent business development efforts. - Personally invested in Kahoot! which is now a $2.4B company

Early Investor

2018 - 2020

Invested personally in Kahoot! In their Series A back in 2018. Kahoot! is now a public unicorn company and pioneer in the edtech space.

Board Member & Investor

2012 - 2018

VP of Product Marketing

2005 - 2007

I led brand positioning to capture funding for a rapidly growing start-up company (50M to 100M views per month). Directed development of collateral materials and presentation decks. - Played critical role in securing $20M in funding for the company. Introduced the funding source (Trinity Ventures) to the founder and CEO; assisted in the presentations and negotiation process. Enabled rapid growth for the company that was subsequently sold to News Corp for $300M cash. - Garnered positive PR for the company, including launch in TechCrunch that created a significant amount of publicity (including article “Photobucket Controls Two Percent of the Internet”).

Director of Category Management

2001 - 2005

I initially served as the category manager for electronic equipment, with a $500M gross merchandise value. Subsequently became the director of new categories, with a focus on building these categories either internally or via acquisition (e.g. Education, Tickets, Classifieds). Played critical role in attempt to acquire MercadoLibre, including trips to Sao Paulo and Buenos Aires to engage in the bid process. Additionally, served as a consultant for eBay’s acquisition of StubHub, providing recommendations on deal completion strategies. Built the Electronic Equipment category to the highest-growing category at one point during tenure. Specific product launch successes included: - Led the build-out of a product that drove a significant improvement in revenues (fostered partnership with CNET on product that enabled sellers to use a catalog from CNET). - Launched “Cell Phone Configurator” product that eased the process for individuals to list their cell phones on eBay, resulting in a substantial category revenue increase.

Founder & Senior Director of New Products

1999 - 2001

I co-founded and launched company that served as a marketplace for electronic equipment. I created the business plan from scratch and delivered pitches to VCs, which led to our successful $10M Series A and B funding from Mohr Davidow and Trinity. I spearheaded business development efforts, including development of the inside sales model, and hired, trained, and managed a team of 7 direct reports. Played a key role in growing the company in from a concept in my apartment to $15M in revenue in just 2 years.

Corporate Development

1998 - 1999

I served as a Chief of Staff to the CEO. I attended Board meetings and prepared Board decks. I assisted the CEO in navigating through the entire IPO process, and facilitated discussion between Morgan Stanley and Portal.

Investment Banking Analyst, Mergers & Acquistions

1994 - 1996

I completed the Analyst Program within the M&A Department. I created complex models that contributed to the consummation of $10B+ in acquisitions.