CASE STUDY: Scaling a Team to IPO

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The Building of an IPO Team


As a healthcare technology start-up in 2008, Castlight Health was establishing its executive level team.  With Calibre One’s guidance and insight, the company began building its team with a VP Engineering and a VP of Product Marketing.  The remainder of the team was built over the following four years with the addition of a COO, CMO, CFO, and VP of Professional Services.

From Start-up to $1B

After securing a venture round of funding, Castlight Health began recruiting for executives to help scale the company and support the growth of its product.  In late-2009, Calibre One launched a VP of Engineering search to target candidates with the ability to scale the healthcare platform during its early growth stage.  Simultaneously, an executive search for a VP of Product Marketing was conducted to provide strategic and tactical leadership of the marketing of the product.

In June 2010, the start-up raised its Series A round of funding and the need for organizational support was immediate.  Calibre One launched a Chief Operating Officer search for the company to rapidly scale and meet market demand.  This included the management of service levels, internal processes, team composition, culture, and products.  The following year, a Chief Marketing Officer search began to lead the functions of enterprise marketing, corporate marketing and communications.


At the same time that Castlight was securing its final round of funding, the search for a Chief Financial Officer was under way.  Calibre One was tasked with finding the ideal candidate to support the company as it heads towards a major liquidity event.  Shortly after securing a $100 million Series D round, the target candidate was hired and the company began positioning itself for a S1 filing.

The final searches before the company’s IPO were a VP of Professional Services to maintain the support of the sales team and a Sr. Director of Product Management and a new VP of Engineering to support a period of rapid and sustained growth.  The company’s initial VPE had a preference for small, start-up cultures and was no longer a fit as the company grew.

Post-IPO, Calibre One continues to build out Castlight Health’s executive team within the HR, strategy, and general counsel functions.

Unique Attributes

The line-up of dynamic and successful executives that were placed onto Castlight Health’s team did not have healthcare technology backgrounds. Calibre One targeted candidates within software-forward companies like Adobe, Model N, and Advent and SaaS companies like SuccessFactors and Jigsaw with consulting backgrounds.