Roundtable discussions aimed towards growing long-lasting relationships with other influential leaders across the US
Research-driven thought leadership on people experience design and strategy tailored, tailored towards the workforce of 2022
Best practice collaboration to equip your organization with people-improving factors to succeed this year
We'll keep things fairly informal, but will make sure to cover the following:
Introductions and a brief spotlight on Greg Leos, GM and Head of Payments at Weave (NYSE: WEAV), to stage the conversation.
Group roundtable discussion focused on how CROs are balancing investment in AI/tooling with developing problem-centric rep skills, manager-led coaching, and a buyer-first operating system to drive consistent performance and predictable growth.
Q&A and peer collaboration where leaders compare what is actually working to turn tech stacks and training programs into a scalable GTM performance system their teams can run every day.
Greg Leos is the General Manager and Head of Payments at Weave (NYSE: WEAV), where he leads the company’s payments business serving the healthcare sector. Previously, he has held senior executive roles across the fintech and cybersecurity industries, including Chief Revenue Officer at VikingCloud and leadership positions at Fiserv, Worldline, Trustwave, and Sysnet. In these roles, he has led global sales team, worked with Private Equity and participated in two company exists (combined value of $2B). Active in industry leadership and philanthropy, Greg has served on multiple advisory boards supporting early-stage startups, and has held board positions with several nonprofit organizations.
Keenan is a respected sales expert and founder of A Sales Guy, a Sales Training and Consulting firm specializing in driving real sales results in the digital age. He is known for his dynamic speaking style and has made a significant impact at events like Inbound 2018. Keenan is the author of multiple books, including "Not Taught", "Gap Selling," and soon to be "Gap Prospecting" (Jan 2026 release) which explore modern sales techniques and Problem-Centric™ selling. His methodology focuses on putting the buyer at the center of the sales process and helping them recognize the value in addressing their problems. Keenan's approach emphasizes the importance of understanding customer needs, asking insightful questions, and demonstrating how products or services can bridge the gap between current and desired states.
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Celeste is a Gap Selling–Certified Training Partner and the co-founder of Sales On Tap, working with underperforming sales teams to lift win rates and drive revenue through a Problem-Centric™ approach. With 18+ years of experience leading hospitality sales teams, she now trains sales teams across multiple industries on how to diagnose business problems, quantify impact, and drive measurable revenue outcomes. Her awards and accolades include Manager of the Year for Marriott, Sales Director of the Year, the Triad Business Journal 40 Under 40 Award, the GOAT Award, and being named one of Denver’s Top 15 LinkedIn Trainers in 2023. Celeste’s work focuses on uncovering the business problems that stall revenue growth and giving teams the skills, coaching, and reinforcement to fix them. She’s known for her straightforward style and her ability to take a team from “lots of activity” to measurable, predictable outcomes.
ASG understands the true root causes to the key problems behind long sales cycles. We know the difficulty of growing or maintaining your ASP and what impacts your win rates and why it’s difficult for most organizations to maintain a 30% win rate or better. Most importantly, we know how all these challenges impact the ability of sales organizations to make quota and accelerate sales growth.
We help GTM Organizations align with how today’s buyers buy – giving you confidence in your sales motions, your forecasts, and your revenue objectives. Most firms train reps how to sell. We build the problem-centric operating system that ensures they can.
