If every rep had a digital coworker to prep calls, update CRM, and draft perfect follow-ups—what would your team do with the time back? Robert Henderson (Head of Revenue, AskElephant) breaks down AI orchestration for sales & CS, why “proactive AI” beats prompt-and-pray, and how leaders can coach in near-real-time.

What you’ll learn:

• What an AI orchestration platform actually does for sellers, CS, and leaders
• How custom agents (“digital workers”) automate prep, notes, CRM hygiene, and follow-ups
• Building a deal-intervention agent that alerts managers when a call goes sideways
• The future: proactive AI that acts before you ask
• The leadership system Robert uses: a Personal Priority Roadmap aligned to company goals
• Big mistakes teams make rolling out AI—and how to avoid siloed chaos

Key takeaways:

• AI should make humans more human: deepen connection & decision-making.
• Treat agents as digital workers you hire/train to your playbook.
• Move from reactive “prompting” to proactive AI aligned to your customer journey.
• Align leadership with a public personal roadmap to enforce focus.

Resources mentioned:

Multipliers by Liz Wiseman

Designing Your Life by Bill Burnett & Dave Evans

Connect with Robert Henderson https://www.linkedin.com/in/robert-henderson/
Connect with AskElephant: https://www.askelephant.ai/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

#Sales #CustomerSuccess #AIinSales #RevenueOperations #SalesLeadership #SalesAI #ProactiveAI #DigitalWorkers #AIAgents #CRMAutomation #RevOps #AskElephant

In this episode of The Future of Selling, host Rick Smith is joined by Michael Gallagher, founder of the Stevie Awards and co-founder of two AI-driven companies: Reqsy and ImageShield.

Michael shares why recognition matters more than ever in an AI-powered world, how storytelling is the key to standing out, and why building your personal brand is crucial—especially for early-career sales professionals facing automation threats.

🔥 Key Topics:

Why Michael launched the "Oscars for Business" in the shadow of Enron

How AI is changing sales recognition—and how to use it wisely

How to tell a story that gets noticed (and wins awards)

Advice for sales reps who want to future-proof their careers

💡 Whether you’re a seller, a team leader, or just curious about the future of recognition and AI, this conversation will leave you with clear, practical takeaways.

Connect with Michael Gallagher https://www.linkedin.com/in/michael-gallagher-a8b785/
Nominate a Sales Pro for a Stevie Award: https://stevieawards.com//sales

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

Cold outreach is broken—and this founder has a plan to fix it.
In this episode of The Future of Selling, we explore what happens when you stop spamming inboxes and start respecting your prospects.

Our guest is Ryan O'Hara, founder of Pitchfire, a paid-prospecting platform that flips traditional sales outreach on its head. Instead of begging for time, reps pay for responses—and it’s working. With reply rates up to 60% and meetings booked in just 3 pitches, this is not your average cold outreach conversation.

🎯 We cover:
– Why reply rates have plummeted and how to turn the tide
– The difference between buying a meeting vs. buying a response
– How creativity (like sending piano songs!) builds trust
– What “zero-click marketing” and personal branding mean for sellers
– Why paid prospecting could actually be more ethical
– The future of B2B sales, AI, and buyer-led deal rooms
– A real story about how a cold call led to a life-changing conversation

Whether you lead a sales team or carry a quota, this conversation will challenge the way you think about outreach.

Connect with Ryan O'Hara https://www.linkedin.com/in/ryanmohara/
Connect with Pitchfire https://www.pitchfire.com/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/