Securing Megadeals requires more than just a strong pitch. It demands a deep understanding of deal orchestration and stakeholder management.

In this episode, Bora Brännström, the co-founder of Megadeals Advisory, joins Alex Raymond to share insights on navigating the complexities of large, multi-million dollar contracts. Bora breaks down what makes a deal truly complex, from influencing decision-makers at every level to managing a web of cross-functional relationships. He points out a common challenge many companies face—rainmaker dependency—and how relying too heavily on a few key individuals can hinder growth, especially for scale-ups.

So how can account managers scale success in such a high-stakes environment? Bora points out the importance of proactively engaging with multiple stakeholders, leveraging internal references, and using targeted media to build trust across the organization. Can a systematic approach to deal orchestration be the key to driving consistent growth? Bora and Alex’s discussion offers strategies for anyone looking to step up their game in managing complex deals and building stronger relationships with key stakeholders.

Episode Breakdown:

00:00 Introduction

02:19 Defining Megadeals

04:44 Four Criteria of Complex Deals

07:03 Challenges in Scaling Sales Teams

10:13 Finite vs. Infinite Markets

14:45 Expanding Within Existing Accounts

17:31 Stakeholder Mapping

20:52 Ideal Stakeholder Map (ISM)

25:35 Accessing Key Decision Makers

30:40 Proactive Account Management

34:54 Actionable Steps for Account Managers

40:58 Building a System to Eliminate Rainmaker Dependency

43:40 Specialization and Support for Rainmakers

Links

Connect with Bora Brännström:

LinkedIn: https://www.linkedin.com/in/bora-br%C3%A4nnstr%C3%B6m-a193a9a/

Website: https://www.megadeals.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Most companies treat onboarding like a finish line, but it’s the starting gate for retention, customer success, and long-term revenue.

Alex Raymond welcomes onboarding expert Donna Weber, the author of “Onboarding Matters,” to challenge the idea that implementation equals success. If a customer isn’t using a product in a meaningful way, does it even matter that they have access to it? Donna explains why the first 90 days determine whether a customer sticks around or drifts away, and how her orchestrated onboarding framework helps companies guide customers to real value, not just a completed setup.

Donna also breaks down a common mistake: declaring victory too soon. Product deployment isn’t the finish line. Without quick wins and clear adoption, customers second-guess their decision, leading to churn. Donna shares ways to shift the focus from closing deals to building long-term success, with insights on user adoption, time to value, and the hidden cost of bad onboarding.

A must-listen for account managers and customer success teams who want to turn onboarding into a growth strategy.

Episode Breakdown:

00:00 Introduction

01:46 The Critical Role of Onboarding

04:36 Onboarding vs. Implementation

06:23 Declaring Victory Too Early

09:42 Defining Onboarding: The Orchestrated Onboarding Framework

11:05 Review and Ongoing Optimization

14:09 Delivering Quick Wins

17:08 The Concept of Buyer's Remorse

19:10 Quick Wins vs. First Value

22:33 Trade-offs in Onboarding Approaches

24:29 Value Journey and Team Structure

26:14 Applying Onboarding Concepts Beyond SaaS

30:46 Incentives and Long-term Profitability

34:31 Team Structure and Responsibilities

37:04 Measuring Success in Onboarding

41:59 Linking Metrics to Business Impact

43:25 Key Takeaways for Successful Onboarding

Links

Connect with Donna Weber:

LinkedIn: https://www.linkedin.com/in/donnaweb/

Website: https://www.donnaweber.com/

https://www.donnaweber.com/post/accelerate-success-the-power-of-quick-wins-in-customer-onboarding

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

RevOps is more than a back-office function. It is a game-changer for sales operations, account management, and long-term revenue growth.

Alex Raymond sits down with Katherine Nino, the head of global revenue operations at Makosi, to talk about how RevOps goes beyond traditional sales enablement and shapes the entire customer lifecycle. They discuss the power of client health scores, how data-driven insights help account managers stay ahead of churn, and why a culture shift around risk and collaboration is essential.

Katherine shares her approach to building a health score model that cuts through data overload and makes it easier for teams to focus on relationships. She also challenges outdated views on sales handoffs, training, and accountability, making the case for a more connected approach to retention and growth.

Join Alex and Katherine’s discussion to discover a clear roadmap for leveraging RevOps to improve client satisfaction, reduce churn, and drive sustainable revenue growth.

Episode Breakdown:

00:00 Introduction

01:53 What is RevOps?

03:07 Strategy and Transformation

05:05 Data Structure and Reporting

08:20 Evolution of RevOps

10:10 Orchestration and Collaboration in RevOps

14:42 Building a Client Health Model

18:39 Proactive Client Management

20:01 Developing and Testing the Health Model

24:00 Implementation and Success of the Health Model

27:31 Role of Account Managers in Using the Health Model

32:10 Improving Data Quality and Compliance

38:08 Mindset Shift for Account Managers

42:52 Regular Data Hygiene Practices

44:03 Importance of Training and Development for Account Managers

Links

Connect with Katherine Nino:

LinkedIn: https://www.linkedin.com/in/jkatherinenino/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Most companies chase new customers without realizing retention is where real growth happens. Bob Mathers joins Alex Raymond to share why the smartest businesses focus on keeping customers for five years and how the right strategy can turn retention into a competitive advantage.

In this episode, Bob breaks down the 5-Year Customer Model and explains why high churn is often a sign of deeper problems. Are companies setting themselves up for long-term success, or are they still stuck in outdated sales-driven models? Bob challenges leaders to rethink how they structure teams, run QBRs, and measure success. Instead of leaving retention to customer success teams alone, he lays out a case for making it a company-wide effort.

Bob and Alex’s discussion is a must-listen for account managers and business leaders ready to move beyond quick wins and start playing the long game.

Episode Breakdown:

00:00 Introduction

02:08 Bob Mathers’ Journey to Customer Success

04:52 The 5-Year Customer Model

05:03 Frustration with Customer Success Conversations

06:06 Shift from On-Prem to SaaS Models

08:10 The Burden of Generating Value

09:09 The Role of Customer Success in Long-Term Retention

11:35 The Role of Customer Success Managers

14:48 The North Star Goal: Five-Year Customer Retention

17:04 Ideal Customer Profile and Marketing Alignment

20:03 Commitment to Long-Term Goals

21:08 The Role of the CEO in Driving Change

22:02 Single-Digit Incremental Improvements vs. Mindset Shift

25:09 Core Functions, Behaviors, and KPIs

26:46 The Role of Data in Customer Success

27:18 Is a 5-Year Customer Good Enough?

28:06 The Role of the Chief Customer Officer

29:00 The Future of Customer Success and CCOs

32:32 The Role of Product in Customer Success

35:05 Optimal Structure for Customer Success Teams

39:48 Closing

Links

Connect with Bob Mathers:

LinkedIn: https://www.linkedin.com/in/bmathers/

Website: https://bobmathers.ca/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Customer success is at a crossroads. Does it need a complete rebrand? A new strategy? A bigger role in driving revenue?

In this episode, Alex Raymond talks with Rav Dhaliwal, a veteran in customer success and account management, about what’s working, what’s broken, and what needs to change. Rav shares why customer success teams struggle to define their own value and how that disconnect affects both customers and company growth.

One of the biggest challenges? The divide between sales and customer success. Both teams focus on helping customers see value, yet outdated structures keep them working in isolation. Rav explains why shared goals and incentives could create stronger results for everyone.

Rav also questions whether the term “customer success” still makes sense. Is it time to rethink the function entirely? Should it evolve into something bigger? If customer success is truly a competitive advantage, leaders need to stop treating it as an afterthought.

This episode pushes past buzzwords and into the real conversations happening inside companies today. If you’d like to know where customer success is headed, this is one you don’t want to miss.

Episode Breakdown:

00:00 Introduction

01:55 Rav’s Career Journey and Insights

02:57 The Evolution of Customer Success

06:19 Linking Customer Success to Revenue

08:17 Incentives and Organizational Alignment

09:11 Misconceptions About Customer Success

10:09 The Need to Retire the Term “Customer Success”

13:05 The Future of Customer Success

15:26 Customer Success and Revenue Ownership

19:30 Organizational Design: CCO vs. CRO

22:39 Skepticism About the CCO Role

25:05 The Importance of a CCO in Complex Organizations

29:40 Typical Friction Points in Alignment

35:04 The Competitive Advantage of Great Customer Success

37:04 Integrating CS into the Sales Process

42:15 Growing the Deal with CS Involvement

Links

Connect with Rav Dhaliwal:

LinkedIn: https://www.linkedin.com/in/ravinderdhaliwal/

Medium: https://ravsterd.medium.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Drowning in unrealistic expectations? If “hero mode” feels like your default setting, it’s time for a reset.

Rachel Provan, a customer success leader turned coach, joins Alex Raymond to discuss why so many account managers are expected to operate at peak performance with fewer resources and more demands. She breaks down how to push back effectively, set real priorities, and communicate workload challenges without feeling like you’re making excuses.

This episode digs into the mindset shifts that help account managers move from constantly defending their role to confidently leading client conversations. Rachel also challenges the way we approach QBRs, arguing that they should be more than a routine box to check.

Want to be seen for the impact you make? Start tracking your wins, speaking up, and claiming your seat at the table. Alex and Rachel’s discussion gives you the strategies to do exactly that.

Quotes

• “If you ask me to do the work of 10 people, I physically cannot do that. So what I advise people to do is really to look at what are the things that I have to get done? What’s the outcome that we need? Get really, really clear on priorities with these people, with whoever your boss is.” (03:54 | Rachel Provan)
• “We have this sense of this idea of time management that if we somehow time box and figure out the right order of things and do enough planning, we’ll somehow be able to fit 10 pounds of potatoes into a five pound bag. And time is fixed. There’s no managing it. So it’s really all about prioritization and being realistic across the board.” (09:53 | Rachel Provan)
• “The number one thing that I advise people to ask their teams, especially if you’re going in there for the first time, if you’re having your first one-on-ones with people, my favorite question for them is: Do you feel your work here is valued? That is the number one question that will tell you if they’ve got one foot out the door, if they’re checked out. Because if they don’t feel their work is valued, what’s the point?” (11:11 | Rachel Provan)
• “If people aren’t giving you recognition, it’s not necessarily because they think you’re crap at your job. They’re thinking about themselves. They’re not thinking about you. They’re not keeping track of what you’re doing. I encourage everyone to keep an accomplishment tracker.” (36:45 | Rachel Provan)

Links

Connect with Rachel Provan:

LinkedIn: https://www.linkedin.com/in/rachelhprovan/

Website: https://provansuccess.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Most account managers are told to ask great questions, but without trust, those questions go nowhere. So how do you earn the right to dig deeper without losing credibility?

In this episode, Alex Raymond is joined by Richard Harris, the founder of the Harris Consulting Group and author of “The Seller’s Journey,” to discuss how emotional intelligence helps account managers earn the right to dig deeper without losing trust. Richard introduces the “respect contract,” a way to set the stage for better client conversations.

This episode also explores why focusing on economic impact is the best way to drive urgency and meaningful engagement. Along the way, Richard challenges common sales advice and shares practical strategies for handling disengaged clients, navigating tough conversations, and strengthening relationships. If you’ve ever struggled to get real answers from a client, Alex and Richard’s discussion will give you the tools to change that.

Quotes

• “In sales—and even in account management after they become a customer—our job is to keep earning our customers’ trust.” (03:22 | Richard Harris)
• “If leadership hasn’t taught them to send an email before you ask those questions, well, that’s just piss poor leadership, in my opinion. That’s just terrible leadership.” (09:54 | Richard Harris)
• “Nothing drives urgency more than money. Nothing.” (27:25 | Richard Harris)
• “You don’t become more resilient by doing the same thing over and over again. You become more resilient because you try something and you adjust.” (31:35 | Richard Harris)

Links

Connect with Richard Harris:

LinkedIn:https://www.linkedin.com/in/rharris415/

Website: https://theharrisconsultinggroup.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm

Most customer success strategies miss the mark because they push a product instead of solving real customer pain points. So how do you keep clients engaged and drive real growth?

Alex Raymond sits down with Emilia D’Anzica, the Chief Customer Officer and founder of Growth Molecules, to discuss what makes customer success work. Emilia shares why leaders struggle to get buy-in, how silos kill momentum, and why clear roles and accountability matter more than ever. She also challenges companies to rethink their approach—are they equipping teams to drive retention, or just expecting results without the right tools?

From using AI to lighten the load on account managers to the shift in how investors view customer success, this episode has insights for leaders who want to build stronger, more sustainable client relationships.

Quotes

• “Stop trying to push your whole product on a client. No one cares about your product. They care about what the product is going to do to help alleviate their pain.” (43:31 | Emilia D’Anzica)
• “1st, what’s the company’s North star? What’s our organization doing in this grand scheme of things? And then what’s in it for the individuals who are going to make it possible? If you aren’t answering those two questions around the why, the why for the company, the why for me, then people can quickly get lost or working in silos. And I think that’s really important, understanding the big picture and then breaking it down into micro steps to success. And that’s where I would start as a leader.” (​​04:28 | Emilia D’Anzica)
• “I cringe when people say everyone owns customer success or everyone owns this goal that the company’s achieved. Actually, no, you need to break it down and really explain who owns the function.” (06:58 | Emilia D’Anzica)
• “The one thing you can’t automate with tech is making sure that people feel like they’re part of the mission and the change, and that you’re enabling them during change.” (10:17 | Emilia D’Anzica)

Links

Connect with Emilia D’Anzica:

LinkedIn: https://www.linkedin.com/in/emiliadanzica/

Website: https://growthmolecules.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

Podcast production and show notes provided by HiveCast.fm