One February a few years before Okta’s IPO, the energy at “SKO” (sales kickoff) was electric. An enterprise AE had hit his entire annual quota in the first week of the fiscal year on a single transaction, and closed the deal on the sidelines during SKO. Ben Horowitz (our Board Member and one of our first investors) did an inspiring fireside chat with Frederic Kerrest, our Co-Founder and COO. And then to close the week Freddy addressed the entire sales org to rally the troops, and it felt like the roof was going to come off of the building. He pointed out that we were all building something new, and that’s never easy: “If you want something easier – HP’s hiring!”. It brought the house down.
January and February usually means that it’s both annual planning season – when leadership teams set up the business financial and operational goals for the year – as well as sales kickoff or SKO season in enterprise businesses. So it feels timely to write about SKO as one of my first posts.
Whether a B2B founder starts out by building a sales team, or they lead with a bottom-up GTM and add a direct sales team later, eventually any B2B business (and even developer-led products) that aspires to get very large will need to invest in a top-down sales motion. If the market is big enough, “a bottom up GTM is not enough to unlock the full potential of a market.”
SKO – and its quarterly cousin, the “QBR” – is in many ways the ultimate manifestation of this approach to GTM. While the experience has certainly been dramatically changed in the last 2 years due to COVID, SKO is a critical part of the cadence of enterprise software businesses. It’s the primary forum for “the field” and “HQ” to come together, build relationships over multiple days without the demands of attending to customers, and learn what is in store for the coming year. An enormous amount of work goes into a properly-executed SKO, particularly for functions like sales ops, sales training and enablement, product marketing, and pricing and packaging. SKO also is often the venue where company leadership, and certainly sales leadership, sets the tone for the entire year. SKO often also involves an analogous “kickoff” for engineering teams as well (“EKO”) and for the company overall (“CKO”).
When I joined Okta in 2013, I was new to operating in startups and technology, so the entire SKO experience was new to me and I tried to learn as quickly as I could and soak it all in.
One of my first observations is how “SKO” evolves as the company evolves, particularly if you are fortunate to be a part of a rocketship business like Okta. My first SKO experience was with maybe a couple dozen sales reps, sales engineers, and managers, in a small hotel lobby a few blocks from Okta’s offices in SoMa in SF. Contrast that modest first experience with how Okta – and other scaled enterprise businesses – manage SKO today, which is often at a massive stadium-like venue, in a different city, with thousands of attendees, and often with strategic partners invited as well (as they are a part of the “army of sellers” an enterprise business needs to win at scale).
Another observation was participating in sales training directly. I was focused on building technology partnerships and so wasn’t a quota-carrying rep, but we worked very closely with the field in those days, and our team’s leadership wanted to ensure we all understood how to position Okta. The “challenger sales” methodology we learned that day has stuck with me ever since.
Finally, SKO creates an energy and momentum that carries through the entire business – not just sales and marketing, but product and engineering and ops/G&A as well, that inspires everyone to give it their all in the coming year. The way I have described SKO from our early days at Okta to others is that the people in the room have a “secret” – “we know how big this product and business is going to be, but the rest of the world doesn’t yet, and it’s our job to share this with them.” Talk to someone at any recently-public or soon-to-be-public enterprise business – Snowflake, Databricks, Datadog, Confluent, etc – and the teams gathering for SKO at these events will surely tell you something similar.
Whether you are product-centric or GTM-centric, B2B founders should embrace SKO. It’s a rare opportunity to bring everyone together in-person (even more important now in the COVID/remote-first era), celebrate past wins and standout achievement by individuals and teams, and communicate ambitious goals for the year – which you’ll then crush and then celebrate at next year’s SKO after you raise the bar again :)
My friend Rishi Taparia recently interviewed me for his Tippets by Taps newsletter. If you’re interested in learning more about my story, and a few thoughts on M&A in high-growth tech companies, check out the post here.
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I miss being at a SKO this year. It’s been such a ritual to kick off a new beginning. Learnings, seeing peers from around the world, motivating leadership. So many positives when they are done right.