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.

Subscribe to The Revenue Insiders and follow us on LinkedIn for more practical insights on sales leadership, enablement strategy, and modern GTM execution.

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.

TL;DR

Sales enablement pioneer Roderick Jefferson joins Kelly Lewis for a raw, deeply human conversation about the evolution of enablement, why revenue teams are still missing the mark, and the life-altering stroke that forced him to redefine success, leadership, and self-care.

If you work in enablement, revenue, or leadership, this episode is required listening.

What happens when the person who coined the term sales enablement says he is no longer a fan of it?

In this episode of The Revenue Insiders, Kelly Lewis sits down with Roderick Jefferson, widely known as the grandfather of sales enablement, for a conversation that goes far beyond job titles and frameworks.

Together, they unpack why enablement has outgrown its original definition, how revenue enablement should function as the connective tissue across go to market teams, and why roles like Customer Success, Professional Services, and onboarding are still treated like distant relatives instead of critical partners.

Roderick challenges the profession to stop being myopic, stop operating at the kids table, and start speaking the language of revenue, relationships, and impact across the full buyer and customer journey.

But this conversation takes a powerful turn.

Roderick opens up about his personal story behind his book Stroke of Success, sharing how unchecked stress, ego, and ultra achievement led to a massive stroke that nearly cost him his life. What follows is an honest reflection on burnout, identity, leadership, and the dangerous normalization of living at the red line.

Kelly and Roderick discuss:

• Why enablement must evolve beyond sales and truly serve the full go to market ecosystem

• The role of enablement as translators across marketing, product, sales, CS, and services

• Why team selling is an overlooked core competency

• The hidden cost of being an ultra achiever

• How redefining success can literally save your life

• Why self-care is not a reward, but a daily responsibility

This episode is a reminder that success and happiness are not the same thing, and that the best leaders know when to step back, trust their people, and take care of themselves.

If you have ever felt exhausted, stretched too thin, or unsure how long you can keep pushing, this conversation will stay with you.

🎧 Listen now and join the conversation.

👉 Subscribe to The Revenue Insiders for more candid conversations on modern GTM leadership.

👉 Follow https://www.linkedin.com/company/the-revenue-insiders on LinkedIn for behind-the-scenes insights and discussions.

👉 Connect with Roderick: https://www.linkedin.com/in/roderickjefferson/

TL;DR:

Leadership does not mean choosing between empathy and authority. In this episode, returning guest Raheela Nanji joins Kelly Lewis and Tiffany Jones to break down feminine energy in leadership, why empathy is a learnable skill, and how strong leaders hold boundaries without becoming pushovers.

What does it really mean to lead with feminine energy and why does it still feel uncomfortable for so many leaders?

In this episode of The Revenue Insiders, Kelly and Tiffany welcome back executive coach Raheela Nanji for a deep, honest conversation about leadership styles, authenticity, and the evolution of how leaders show up at work.

Together, they unpack:

• Why feminine energy is not about gender, and why everyone has access to it

• The difference between empathy and being “soft”

• Why empathy is a learnable leadership skill, not a personality trait

• How leaders can use intuition, active listening, and creative questioning to diffuse high-pressure conversations

• Why boundaries and feminine energy are not mutually exclusive

• How to experiment with new leadership behaviors using small, safe, 1 percent changes

• Practical tools like “I like, I like, I wonder” for navigating executive conflict

• How generational shifts and COVID reshaped expectations of leadership

Raheela shares insights from coaching leaders around the world, along with real examples of how leaning into instinct, curiosity, and empathy creates better outcomes for teams and organizations.

This episode is especially relevant for GTM leaders, enablement professionals, and anyone navigating leadership growth while trying to stay authentic to who they are.

If you have ever wondered:

• Do I need to change who I am to move into executive leadership?

• Can I lead with empathy and still be respected?

• How do I hold boundaries without being labeled difficult or a pushover?

This conversation is for you.

🎧 Subscribe to The Revenue Insiders for more candid conversations on leadership, growth, and modern GTM careers.

📲 Follow The Revenue Insiders on LinkedIn for behind-the-scenes insights and clips from each episode.

-Article Mentioned by Raheela

https://hbr.org/2025/04/empathy-is-a-non-negotiable-leadership-skill-heres-how-to-practice-it

-Connect with Raheela at [email protected]

Guest

Megan Fletcher: @CRMbestie on Tiktok & Instagram

Summary

In this engaging conversation, Tiffany Jones and Kelly Lewis interview Megan Fletcher, a TikTok sensation known as CRM Bestie. They discuss her journey in creating content focused on RevOps and sales, the challenges of balancing a corporate career with family life, and the unique perspective she brings as a woman in a male-dominated industry. The discussion also touches on the importance of empathy in the workplace, the dynamics of remote work, and how personal experiences shape professional interactions. Megan shares insights on efficiency, prioritization, and the value of being a working parent, making this a relatable and inspiring episode for listeners.

Takeaways

• Megan Fletcher is known as CRM Bestie on TikTok, focusing on RevOps and sales.
• Creating digestible content helps salespeople understand complex systems.
• Balancing work and family is achievable with proper prioritization.
• Being a working mom provides unique perspectives in corporate settings.
• Empathy in the workplace is crucial for understanding diverse experiences.
• Remote work can enhance productivity and family time.
• Efficiency is key in both personal and professional life.
• Women in male-dominated industries can leverage their unique perspectives.
• Setting boundaries helps manage multiple responsibilities effectively.
• Engaging with followers on social media fosters community and support.

Keywords

CRM, TikTok, RevOps, Sales, Work-Life Balance, Remote Work, Women in Business, Empowerment, Efficiency, Professional Development

Revenue Insiders host Tiffany Jones sits down with Anders Krohn, CEO and founder of Kernel.ai, to unpack how “agentic company data” is transforming RevOps at high-growth companies like Navan, Gong, and Mistral by finally fixing broken CRM data at scale. They dig into why most revenue leaders don’t trust their Salesforce or HubSpot account data, how Kernel’s AI-native alternative to Dun & Bradstreet cleans duplicates, builds accurate corporate hierarchies, and turns your CRM into a true source of truth for planning, routing, and territory design. If you care about account hierarchies, TAM coverage, and deploying AI on clean data instead of “garbage in, garbage out,” this episode is a must-listen—learn more about Anders and the team at Kernel at www.kernel.ai.

L;DR: Kelly Lewis and Tiffany Jones kick off 2026 with bold go-to-market predictions: AI agents become a “shadow RevOps team,” ICPs get dynamic and constantly refreshed, pricing shifts away from seats toward consumption and outcomes, hiring prioritizes EQ over resumes, sellers enable champions to sell internally (especially to CFOs), and digital sales rooms evolve into AI-powered deal command centers.

2025 was a roller coaster, but 2026 is already shaping up to be a defining year for modern go-to-market teams. In this predictions episode, Kelly Lewis and Tiffany Jones unpack what they believe will materially change how revenue orgs operate, hire, sell, and enable.

Tiffany argues that AI agents are about to explode inside RevOps workflows, creating a “shadow RevOps org” that handles specialized tasks like territory optimization, scoring, lead flow balancing, and routing. She even puts a stake in the ground: by the end of 2026, a 10-to-1 agent-to-human RevOps ratio will start to become the expectation.

Kelly’s first prediction builds on a common ICP problem: companies define an ICP once, then let it sit for years. With better data and AI, ICPs become living and dynamic, shifting from “who could buy” to “who should buy,” including who can implement, realize value, and expand.

From there, they dig into the ripple effects: what happens to compensation and quotas when RevOps tools move from seat-based pricing to consumption or outcomes? Why will buyer education make old-school consultative scripts feel slow or irrelevant? Why does EQ become the most important hiring trait as AI handles more of the “heavy lifting”? And what does it look like when sellers stop “selling to the CFO” and start enabling their champion to sell internally?

They close with a big bet: digital sales rooms evolve from static link hubs into the AI-powered command center for the deal, where meetings, proposals, and content live together, and buyers can ask the room questions and get instant answers.

If you work in sales, enablement, RevOps, marketing, or revenue leadership, this episode will challenge how you think about your stack, your team, and your 2026 priorities.

Subscribe for more GTM strategy, enablement, and revenue insights, and follow The Revenue Insiders on LinkedIn for weekly takeaways.

Summary

In this episode, Beth Yehaskel, a seasoned revenue architect and go-to-market advisor, shares her insights on building effective go-to-market systems. The conversation delves into the importance of connective tissue in organizations, the challenges of decision-making in smaller companies, and the role of empathy and communication in successful go-to-market strategies. Beth also discusses her approach to consulting, emphasizing the need for testing, iterating, and aligning teams on common goals.

Keywords

go-to-market, revenue architecture, Beth Yehaskel, connective tissue, decision-making, empathy, communication, consulting, testing, iterating

Takeaways

• Connective tissue is crucial for aligning go-to-market systems.
• Decision-making in smaller companies can be complex due to multiple stakeholders.
• Empathy and communication are key to successful go-to-market strategies.
• Testing and iterating are essential for refining go-to-market approaches.
• Aligning teams on common goals helps in achieving better outcomes.
• Understanding the ideal customer profile is vital for go-to-market success.
• Breaking down silos improves organizational efficiency.
• Listening and data analysis are critical in diagnosing system issues.
• Coaching can enhance leadership and decision-making skills.
• Practical and pragmatic approaches build strong foundations.

Sound bites

Connective tissue is crucial. Empathy and communication are key. Testing and iterating are essential. Aligning teams on common goals. Understanding the ideal customer profile.

TL;DR: If you have ever been told “you need to be more strategic” with zero useful guidance, this episode is for you. Kelly and Tiffany break down what strategy actually looks like in your day to day work, how to respond when you get that feedback, and how to rebuild your brand inside the company.

In this solo conversation, Kelly Lewis and Tiffany Jones unpack one of the most frustrating pieces of corporate feedback:

“You just need to be more strategic.”

Fresh off their conversation with Ravi Rajani about executive presence and storytelling, Kelly realizes she has more to say. In this episode, she and Tiffany pull the curtain back on what leaders are really looking for when they call someone “strategic” and why so many high performing middle managers still get labeled as tactical.

You will hear them dig into:

• The difference between having a strategy in your head and being seen as strategic

• Why RevOps and enablement leaders get stuck as “doers” even when they are driving critical change

• How to balance tactical execution with long term business outcomes

• The hidden skill of pre communication and why you must stop sounding reactive

They also share two simple frameworks you can start using today:

• Say, Do, Say: Say what you are going to do, do it, then say it again so the right people see the impact.

• SCOR: Situation, Challenges, Opportunity, Recommendation. A concise way to pitch your ideas with data, business impact, and a clear path forward.

If you have ever:

• Looked around corners and spotted problems early, then got labeled as “negative” or “escalating”

• Been told you are not strategic, without examples or support

• Wondered how to repair an internal brand that has quietly become “too tactical”

Kelly and Tiffany walk through the questions to ask, how to respond in your review, and how to use mentors, resources, and cross functional allies to change the narrative.

They also talk about:

• Personal brand inside your company and why people “remember projects, not tasks”

• Naming and productizing your work so your impact sticks

• What great managers should be doing when they give “be more strategic” feedback

• Why real feedback is a gift, even when it pushes someone to leave for a better aligned role

If you are in RevOps, enablement, CS, marketing, or sales leadership and you want to move from trusted executor to trusted strategist, this episode will give you language, tools, and next steps.