Even though sales enablement as an industry has grown by double-digits over five years — providing new tools and technologies for success — sales teams are failing and missing their goals and sales quotas according to a report by CSO Insights. Based on data from Miller Heiman Group, sales quota attainment dropped more than ten percent over the same five years to 53%.

“The world has changed and people just don’t buy the way they used to,” said Frank Dale, co-founder and CEO of sales playbook software company Costello. “The consumerization of pretty much everything has raised buyers expectations and the information gap has closed dramatically, so as a result sales professionals have to level up and do everything right if they’re going to succeed.”

With an announcement yesterday that his company has raised another $2.1 million in seed funding from strategic investors, Frank is planning on Costello being able to help an increasing number of clients buck the aforementioned downward sales trends and close more and better deals. The fast-growing startup has doubled in size in just the past six months with expectations of doubling again in the New Year.

Investors contributing to the multimillion dollar funding round include:

  • Dundee Ventures (Nebraska)
  • Collina Ventures (Indiana)
  • Irena Goloschokin (CEO of Copper Mountain Technologies formerly of T2 Systems)
  • Social Capital (California/SIlicon Valley)
  • Innovatemap Ventures (Indiana)
  • Elevate Ventures (Indiana)
  • Innovate Indiana
  • Chris Baggott (CEO of ClusterTruck formerly of Compendium and ExactTarget).
  • M25 Group (Chicago)
  • GAN Ventures (Colorado)

“We were fortunate to be an early investor in Costello and are thrilled at the opportunity to re-invest in the company,” said Greg Beaufait, Partner at Dundee Capital. “Costello completely disrupts the way sales teams use traditional call scripts and adhoc tools by providing a solution that allows VPs, sales managers, and sales reps alike to stay aligned and win together.”

Founded in 2017, Costello is pioneering the way organizations build and execute sales playbooks. The platform helps sales reps prepare for calls, ask timely questions, tell relevant stories, and sync insights back to the CRM while showing managers and reps the gaps in every deal so they can work together to move them forward. With Costello, sales leaders can identify what’s working on the frontline and replicate success across the entire team. The infusion of capital will allow the team to accelerate product enhancements such as integrations and customer-requested features, as well as hire new team members to support the growing customer base.

“We live in a world of rising buyer expectations and as a result, we no longer get second chances,” said Frank Dale, Co-Founder and CEO of Costello. “To win, we have to deliver a great experience on every sales call, which is why we need to arm our teams with sales playbooks that cover the critical items. We also need to constantly test and iterate our processes while creating healthy tension between structure and flexibility. These impossible expectations are why we built Costello. We’re delivering a new, powerful way for sales teams to have great conversations every single time.”

Costello counts leading companies like TINYpulse, Sigstr, SalesLoft, Emplify, Guest Supply (a SYSCO company) and 40+ others among its clients. Costello also recently signed its first-ever Fortune 50 client. Having already grown from its original office space at The Union 525 tech community, Costello is outgrowing its second space and awaiting larger digs somewhere else in the building.

From a competitive landscape perspective, the company is mostly competing with “unmet need” and a variety of tools that don’t offer the comprehensive sales playbook approach that Costello does. With this new infusion of funds, Costello has an opportunity to continue its rapid growth and gain market share to a point that by the time the sales enablement software category matures, Indianapolis-based Costello could emerge as the brand of choice.