TL;DR:

Sales Kickoff is not a 3-day event. It is a revenue activation strategy. In this episode, Tiffany Jones and Kelly Lewis break down what makes a modern SKO successful, how to move beyond stand-and-deliver presentations, when to schedule your kickoff, and how to design reinforcement programs that actually change seller behavior.

It’s kickoff season — and if your LinkedIn feed looks anything like ours, everyone is either at SKO, recovering from SKO, or planning the next one.

But here’s the real question:

Are companies reinventing Sales Kickoff… or just repeating the same playbook?

In this episode, Tiffany and Kelly unpack what’s changing in modern Sales Kickoff strategy and what revenue leaders must rethink if they want real impact.

You’ll hear hot takes on:

• Why stand-and-deliver keynotes no longer work for revenue teams

• The ideal timing for Sales Kickoff (and why week three may be the sweet spot)

• When to roll out comp plans (hint: not three days before SKO)

• How to use pre-work and knowledge transfer before your in-person event

• Why small group executive Q&A is more powerful than big stage questions

• How to create intentional executive access moments

• Creative connection tactics like “speed friending” to boost engagement

• The shift from SKO as an event to SKO as a program

Most importantly, they break down what happens after kickoff.

Because the real ROI is not the energy in the ballroom.

It’s the reinforcement that follows.

Kelly shares how to:

• Programmatize post-SKO reinforcement into 5-8 week branded initiatives

• Layer manager coaching development alongside skill reinforcement

• Prioritize what to train first based on business impact

• Use leading indicators, confidence surveys, and behavior data to measure success

Tiffany adds a powerful perspective on measuring “hunger” — how quickly reps engage with follow-up content, request transcripts, and seek more information.

If you’re a sales leader, CRO, Head of Enablement, RevOps leader, or marketing partner thinking about how to make your next Sales Kickoff more impactful, this episode is your blueprint.

Sales Kickoff should galvanize your team.

Reinforcement should transform them.

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TL;DR:

You can’t always “leave politics at the door” anymore. In this episode, Kelly Lewis and Tiffany Jones talk about what happens when world events show up at work, why psychological safety matters more than ever, and how leaders can support their teams without turning the workplace into a debate stage.

We typically don’t talk politics on The Revenue Insiders.

But after a Super Bowl halftime show that sparked national conversation, and in a world where social, cultural, and political moments increasingly bleed into the workplace, we felt this conversation was necessary.

Because whether you like it or not, your team is feeling it.

In this episode, Kelly Lewis and Tiffany Jones explore:

• Why “don’t talk politics at work” is no longer realistic

• The pressure people leaders face in emotionally charged moments

• How psychological safety (yes, Lencioni-style) becomes even more critical

• What real check-ins should sound like (hint: not just “How are you?”)

• The loneliness of leadership — especially for middle managers

• Supporting working parents navigating stress at home and at work

• How to create space without forcing conversation

• Why enabling leaders at every level matters right now

This isn’t about red vs blue.

It’s about emotional intelligence, modern leadership, and recognizing that employees are whole people — not just revenue producers.

We also discuss:

• The ripple effects of layoffs and constant change

• Why middle management often gets overlooked

• How leaders can share appropriately without oversharing

• The power of vulnerability in creating trust

• The importance of best friends at work (and what that does to productivity)

If you manage people, lead a team, or are trying to stay productive in a heavy season, this conversation will resonate.

The world feels fast. Loud. Emotional.

Leadership right now requires more EQ than ever.

You are not alone in navigating it.

🎧 Listen now and join the conversation.

Most companies overlook the secret to dominating cloud marketplaces—and it’s not what you think. As tackle.io CEO John Janke reveals, understanding how AI will reshape go-to-market strategies is the game-changer that can catapult your revenue and valuation in 2024.

In this eye-opening episode, John shares lessons from a decade of navigating the complexities of B2B software sales, acquisitions, and the SaaS explosion. Discover how his team shifted from simply listing on cloud marketplaces to building a multi-component platform that became an essential, must-have tool for industry leaders. You'll learn how to turn channel partnerships into predictable revenue streams, use data-driven storytelling to accelerate deals, and avoid the pitfalls that leave sellers stuck on the sidelines.

We break down the real reason why RevOps can block pipeline, how to empower your sales team with AI agents that demystify customer engagement, and why the future of digital selling hinges on strategic vision and adaptability. Whether you're a CRO, partner leader, or founder, you’ll uncover the keys to positioning your company as a category leader—and making yourself irresistible to acquisition offers.

If you’re concerned about shrinking budgets, fierce competitor landscapes, or the shifting power of marketplaces, this episode will give you actionable insights to thrive. Capital markets are tightening, but the opportunities to stand out and connect with the right ecosystem have never been greater. Don't miss the bold strategies that could define your success in the next phase of SaaS evolution.

Perfect for revenue leaders aiming to double down on their go-to-market approach, product executives preparing for the AI revolution, and anyone interested in the future of digital sales—this conversation delivers the knowledge you need to stay ahead. Tune in now and start reimagining what’s possible in your growth journey.