Creating CEO Playbooks

I love creating agile business systems with my team. When I first became a CEO back in 2000, I had a thesis – you should run your company the same way no matter what size it is (7 people or 7,000 people). My philosophy was that you should always operate as if you’re a day away from being made irrelevant or one day away from becoming #1 in your category….and no matter how many people were in the business, you should treat every person as if they are either a day away from moving on or one day away from creating the most important idea in the company’s history.

Does it really matter if your senior team and you make up almost the entire company (aka you’re pre-revenue and only 6 months in operating history) or if each has 100’s of people under them. Should you run your teams differently?

As business systems go, I enjoy the virtuous circle of “creating and destroying” – meaning that you should always be willing to reinvent something after you’ve created it.

Part of me thinks that even if I can carry in all my tools (playbooks), which I have collected along the way, to each of my companies….they won’t work without heavy customization. So many things change from company to company – a different culture, a different set of buyers and, not to mention, a completely different workforce (that seems to be getting younger and younger).

I was just talking to a peer CEO who is selling compliance products to highly regulated companies. You might think that the typical buyer dynamics at firms like banks hasn’t changed much. If you’re a CEO selling into banks, I think you would agree…that buyer dynamics are changing – regulators are getting tougher, consumers of banking products are more digital, and products/services being sold to the banks are being reinvented. This CEO and I were reflecting that wall street brokers are now Gen-Z (24 years old or less in 2019), using SMS, WhatsApp, WeeChat, and the like, along with Slack….versus the Baby Boomer who is still used to leaving a voicemail and/or email. Do you think compliance is changing to address that change in communication style? Absolutely.


So, if my so-called “playbooks” from my last company are not going to be relevant for my “next team”, why even talk about them? I think it’s about “creating playbooks” for your team, or your company. The idea is to be in the mindset where you apply “create and destroy” playbooks every quarter, no matter where you are in the stage of the company…no matter how much you are struggling or succeeding. Don’t let the “dust settle” and constantly create change.

A peer CEO asked me during an annual retreat this past weekend, “So how do you structure playbooks?” My answer was two-fold:

  1. I like every business function to solution problems in their functional area every quarter
  2. I like the company to solution problems that cut across business functions every quarter

So, I usually structure playbooks into these two categories. We spend time every quarter on “sales”, “product management”, etc. We also spend time every quarter on the “Top 3 issues concerning the company”. And, yes, they do overlap…in a good way.

Playbooks that support advancing your themes

In order to put some structure to the chaos, the ideal is to also create a “painted picture” of the company five years out (that’s a playbook in of itself)…and use the results of that exercise to create a 5-year plan (see below)…which, yes, helps you define your set of quarterly playbooks.

At Janrain, we not only wanted to become the leader in our identity landscape (why have any other goal?)…but we also wanted to define what that landscape would become in 5 years. So we created annual themes supported by quarterly themes, and we unleashed playbooks every quarter. Below are over 170 playbooks (many of them repeated over 11 quarters, and I’m sure I missed a bunch that we launched within a given quarter that were not a part of the original quarterly strategic planning).

We processed three key issues every quarter (again, some repeated until they were actually solved), brought in external consultants to help us see/get past ourselves (17 in total), and participated in some (crazy fun) team building events – every quarter!! See a summary of the team’s playbooks below:

Year Annual Themes Quarterly Themes (# of playbooks)



Execution – With Repeatability




Market Leadership – With Product Differentiation




Growth – With Profitability




Hyper-Growth – With Ecosystem Collaboration

  • Strategic Alliances Investment
  • Industry G2M Specialization
  • Partner Joint Ventures / Dev
  • Mezzanine Capitalization



Revenue Maturity – Maximizing Shareholder ROI

  • M&A (we successfully purchase in an adjacent market)
  • Global Expansion
  • Growth Restructuring
  • IPO Preparation (S1)


External Experts – Educating the Team

Every quarter I run a 3-day offsite QBR. Because I know that my ability to coach/mentor my senior team is limited to my own experiences, management books, and discussions with peer CEOs. So I always leverage outside consultants to help broaden our thinking. I’ll detail my QBR agendas in a future blog. But for now, here’s a key component of those quarterly strategy sessions:

Quarter Theme External Speakers: Education Focus or Theme
1Q16 HighBar
2Q16 Leadership Focus: Finance + Product + Engineering

  • Finance: PacificCrest Securities analyst, Brendan Barnicle, to review what is now the KeyBank SaaS Survey benchmarks that we used to establish targets across the entire business.
  • Product: O’Reilly Media’s VP of Innovation, Roger Magoulas, who at the time chaired the largest Big Data & Analytics conference globally – Strata. He was (and is) one of the most well-connected and knowledgeable people in the “data and analytics space”. We used Roger to establish our thesis around the use of identity data and behavioral analytics as a key differentiator for both marketing and security use cases.
  • Engineering: In addition, as part of early needed transformation, Janrain was a waterfall development shop in desperate need of agile. We invited in Kelley Harris, Agile Consultant & Trainer, who is part of SourceCell. Kelley brought Agile, Scrum, Lean, Lean Startup, Design Thinking, and more to the Janrain team. It was a “religious war” until Kelley came in.
3Q16 Profitable Revenue Focus: Product

4Q16 Business Metrics Focus: Sales

  • Bob Gregoire, a sales strategist and Sandler executive coach, to help us think about our sales model on three axis: Attitude, Technique, and Behavior.
1Q17 Identity Cloud Focus: Customer Success

  • Joshua Fox, who ran the Americas Digital Applications diversified business at CSC. He was one of the more creative guys when it came to account management
2Q17 Data Governance Focus: Professional Services

  • Keith Carlson, “master” of professional services within SaaS companies. Keith started in Andersen Consulting as part of Arthur Andersen. This was before it was spun out to make Accenture. 
3Q17 Identity Analytics Focus: Engineering

  • Invited in Dhruv Bansal. He and Destry Saul had helped us accelerate our data products work at Janrain over the previous two quarters. At the QBR, we summarized that work, which essentially was my way of kicking us in the pants around the data products work I had envisioned back in early 2016.
4Q17 Identity of Things Focus: Product + HR

1Q18 Organizational Strategy Focus: Customer Success + Marketing

2Q18 Offshore Leverage Focus: Sales & Marketing

  • Invited the LBrands CISO, Patrick Reidy. It was a treat to discuss “how to sell to the security team” by talking to the top of the security food chain.
3Q18 Market Development Focus: Europe + Marketing

  • Europe: We invited Mark Danaher to help with our EU business planning and execution. At this QBR Mark and our EU Managing Director presented their work. 
  • Marketing: We also invited the Topo Group (Eric Wittlake) to assist in our marketing benchmark targets, adjustments required to hit those targets, and a management system to monitor and optimize – it’s “Gartner” (aka benchmarks) + “McKinsey” (aka change management) for marketing and sales. 
4Q18 Break Even Operations Focus: Product & Marketing 

  • We brought in Heath Gross, former US counterintelligence agent turned competitive intelligence strategist and CEO of the Sedulo Group (leading Competitive Intelligence consultancy).

Team Building

My playbooks for team-building includes deploying a quarter of “Patrick Lencioni Bootcamp” leveraging his framework taught in “Five Dysfunctions of a Team“. Even though my team would agree that my QBRs are exhausting, we do spend time to have some fun.

Quarter Theme Team Building Events (QBR Fun)
1Q16 HighBar
2Q16 Leadership iFLY, an-HR approved version of skydiving
3Q16 Profitable Revenue Zip-lining at the Pumpkin Zip Tour just outside Portland. 
4Q16 Business Metrics Surfing with Club Ed
1Q17 Identity Cloud Drinking & eating at the Beauregard Vineyards – they have been working the land in Bonny Doon, CA growing premium wine grapes. 
2Q17 Data Governance Hiking at Beacon Rock, one of the most prominent and distinctive geological features in the Columbia River Gorge, and an 848-foot landmark that was once the core of a volcano.
3Q17 Identity Analytics Canoeing at Trillium Lake – a lake situated 7.5 miles south-southwest of Mount Hood in the U.S. state of Oregon.
4Q17 Identity of Things Sponsored tour at Zappos, the experts at delivering happiness.
1Q18 Organizational Strategy Kayaking at Breakwater Cove at 32 Cannery Row, in Monterey, CA 
2Q18 Offshore Leverage Hiking at the Salishan on the coast of Oregon with access to a wonderful Lower Nature Conservancy Trail at Cascade Head
3Q18 Market Development River rafting with the Seventh Mountain River Company on the Deschutes.
4Q18 Break Even Operations Whale Watching on the Riptide.

Here’s a bonus link to my “CEO Management System” in a summary document here.

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.