Accelerating our Painted Picture

“What is our 2024 Painted Picture?”

Yes, “getting to cashflow breakeven” was the goal that we established with the Board on Friday, March 20th. But what the hell did that mean for the business? Questions needed to be answered like: by what timeframe?, with how much capital? and, most importantly, with what changes? We immediately began putting some basic frameworks to work.

Whenever I am, personally, presented with a seemingly overwhelming decision or set of decisions, I draw upon several time-tested frameworks or approaches to decision-making like:

  1. What’s the painted picture?
  2. What are the main strategic pillars?

I was talking recently to one of my past private equity managing director / partners, Brian Peters, at HighBar. We were reflecting on the process, which Brian knew well – one that he was actually beginning to apply to his own portfolio companies.

A Plan in 72 Hours

After that Friday Board call on March 20, how could we establish our plan so quickly, so decisively? It started with a simple view of today vs. 2024. What did we want the business to evolve to, as it was approaching 5x in size? What would it look like in its future steady state?

For those who know me, I learned a long time ago (from one of my “business soul mates”, Surendra Reddy) how to use my portable whiteboard (11 x 17 sheets of paper that I use to brainstorm). Actually, you can find my 3×5 spiral notebooks lying around, along with my three-ring 8.5 x 11 note pad. I’m visual, and like to “think out loud” on various pieces of paper…not to mention with sticky pads.

As you can see above, on that Friday, we looked at the “from -> to” for:

  • Key Financial Metrics (e.g. profitability, direct vs. indirect mix, unit economics, ARR by segment)
  • SMB go-to-market (our shift into other verticals, our move to a reseller centric G2M)
  • MM/ENT go-to-market (more than 90% of our direct sales)
  • Regional go-to-market (50% of ARR globally, 50% of ARR regionally)
  • Customer Success (larger books of business per CSM as we move up market; near/off-shore resources)
  • Prod/Eng (move to omnichannel, externalizing our tools for partners, near/off-shore resources)

Each of my executive team and I worked surgically over the weekend, well into Sunday evening. By 12:30pm Monday we had prepared our new 2020 plan for the Board’s review. And the team nailed it.

In 72 hours from my initial Friday “Team 1 call” to my Monday Board meeting, we had constructed a plan which was not intuitive at first, but after constructed we knew it was right. The Board knew it was right too.

In fact, we didn’t have to iterate, but ratified our strategy and the new 2020 plan on the spot.

The challenge though…we knew that it wouldn’t make sense right away – to our staff, our partners, or or customers….but with the right execution, and the right level of communication, it would allow us to serve our customers better and more economically, while empowering our partner ecosystem almost overnight. It would allow us to optimize the business during the imminent slowdown from Covid-19. It would end up helping us to accelerate our 5-year strategy.

Now, of course, we would have to put together the details and ultimately execute a significant amount of business transformation in only one week – as we targeted April 1st as our day to “accelerate our painted picture”.

Interested in knowing the details of our plan? Our key pillars for change? I’ll provide some insight into that in a future blog.

Jim Kaskade

Jim Kaskade is a serial entrepreneur & enterprise software executive of over 36 years. He is the CEO of Conversica, a leader in Augmented Workforce solutions that help clients attract, acquire, and grow end-customers. He most recently successfully exited a PE-backed SaaS company, Janrain, in the digital identity security space. Prior to identity, he led a digital application business of over 7,000 people ($1B). Prior to that he led a big data & analytics business of over 1,000 ($250M). He was the CEO of a Big Data Cloud company ($50M); was an EIR at PARC (the Bell Labs of Silicon Valley) which resulted in a spinout of an AML AI company; led two separate private cloud software startups; founded of one of the most advanced digital video SaaS companies delivering online and wireless solutions to over 10,000 enterprises; and was involved with three semiconductor startups (two of which he founded, one of which he sold). He started his career engineering massively parallel processing datacenter applications. Jim has an Electrical and Computer Science Engineering degree from University of California, Santa Barbara, with an emphasis in semiconductor design and computer science; and an MBA from the University of San Diego with an emphasis in entrepreneurship and finance.