The Seasons of Sales Enablement

Feb 13, 2026 | Blog

The Seasons of Sales Enablement

For individuals who do what I do (keynote speaker, sales and customer-facing team training and workshops, revenue and sales leadership training), there are seasons. While one may argue it’s another example of short-termism in business, I find it to be not only super appropriate, but something organizations, along with what people like me, should embrace!

The First season: Sales and Revenue Kickoff Season (SKO | RKO)

Since the modern sales profession began in the 1880s, the start of each year is an opportunity to celebrate, communicate, educate, and motivate the entire team for the year ahead.

The header image on this article is a picture from NCR’s 1898 sales kickoff. Attendees were celebrating the release of the 1898 model registers they’d all be selling this upcoming year.

And for me, that means I’m an airplane turd for six weeks, delivering either keynote speeches, delivering workshops for revenue teams, or conducting leadership training. I’ve participated in one of those capacities for twelve different events since mid-December (I’m writing this in mid-February). Four in Dallas, one in Chicago, three in Florida (Ft. Lauderdale, Miami, and Orlando), one in New York, one in Salt Lake City, and two virtual.

The Second Season: Investing and Upskilling Season

It becomes fill-in-the-gaps season, when organizations assess where they want to invest and upskill. Starting this upcoming week, I will begin delivering tailored Four Levers Negotiating workshops, revenue leadership workshops, and messaging choreography programs. This season typically lasts until the end of May.

The Third Season: Quiet Season

It’s summer. While some organizations are focused on the sales leadership upskilling, there’s typically not a ton going on.

The Fourth season: “Last Chance to Hit Our Number” Season

Almost every year, I start getting inquiries in August about programs to help organizations that realize they still have one last shot to upskill their teams and hit their numbers. The most popular of those programs? Four Levers Negotiating! How do we maximize deal value without eroding trust? How do we speed the final mile of these deals?

The Fifth season: Kickoff Design & Planning Season

November and December, I’m playing Tetris in discovery calls, proposals, and preparation for the madness that’s to come in January and February again, trying to make schedules work to help out in as many as possible.

There are plenty of companies that don’t follow a calendar fiscal, so there are random out-of-season things happening all the time, but this is the bulk. So, the first season feels like it’s almost over.

Don’t fight it…embrace it. Start the year inspired, then invest where you need investing. From there, make the halftime adjustments – it’s really never too late, then shift to planning. I love it and embrace it.

With that, I’m going to be laying out how my programs work in an upcoming set of blog articles. A paragraph on a website doesn’t really help you very much, does it? So, keep an eye out for details on:

  • Transparency as a Revenue Superpower Workshops
  • Four Levers Negotiating Workshops (the most popular)
  • Presentation / Formal Messaging Choreography Workshops
  • Revenue Leadership Workshops

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I’m Todd Caponi, CSP®. (<– links to LinkedIn)

I’ve written three books, The Transparency SaleThe Transparent Sales Leader, and Four Levers Negotiating. Available wherever you get your books….in all formats.

I’m a sales keynote speaker and sales trainer, focused on teaching revenue organizations how to leverage transparency and decision science to maximize their revenue capacity.

It’s what I do…teach sellers, their leaders, well…entire revenue organizations how we as human beings make decisions, then how to use that knowledge for good (not evil) in their messaging (informal and formal), sales negotiations, sales presentations, and revenue leadership.

Reach out (email to info@toddcaponi.com) – for inquiries about speaking at your event or sales kickoff, for programs to upskill your customer-facing teams and leaders, or just to nerd out on sales or sales history.

And while you’re at it, sign up for the newsletter, which comes out every other week.

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