Scrum Master Toolbox Podcast: Agile storytelling from the trenches

BONUS: Why Embedding Sales with Engineering in Stealth Mode Changed Everything for Snowflake
In this episode, we talk about what it really takes to scale go-to-market from zero to billions. We interview Chris Degnan, a builder of one of the most iconic revenue engines in enterprise software at Snowflake. This conversation is grounded in the transformation described in his book Make It Snow—the journey from early-stage chaos to durable, aligned growth.
Embedding Sales with Engineering While Still in Stealth
"I don't expect you to sell anything for 2 years. What I really want you to do is get a ton of feedback and get customers to use the product so that when we come out of stealth mode, we have this world-class product."
 
Chris joined Snowflake when there were zero customers and the company was still in stealth mode. The counterintuitive move of embedding sales next to engineering so early wasn't about driving immediate revenue, it was about understanding product-market fit. Chris's job was to get customers to try the product, use it for free, and break it. And break it they did. This early feedback led to material changes in the product before general availability. The approach helped shape their ideal customer profile (ICP) and gave the engineering team real-world validation that shaped Snowflake's technical direction. In a world where startups are pressured to show revenue immediately, Snowflake's investors took the opposite approach: focus on building a product people cannot live without first.
Why Sales and Marketing Alignment Is Existential
"If we're not driving revenue, if the revenue is not growing, then how are we going to be successful? Revenue was king."
 
When Denise Persson joined as CMO, she shifted the conversation from marketing qualified leads (MQLs) to qualified meetings for the sales team. This simple reframe eliminated the typical friction between sales and marketing. Both leaders shared challenges openly and held each other accountable. When someone in either organization wasn't being respectful to the other team, they addressed it directly. Chris warns founders against creating artificial friction between sales and marketing: "A lot of founders who are engineers think that they want to create this friction between sales and marketing. And that's the opposite instinct you should have." The key insight is treating sales and marketing as a symbiotic system where revenue is the shared north star.
Coaching Leaders Through Hypergrowth
"If there's a problem in one of our organizations, if someone comes with a mentality that is not great for us, we're gonna give direct feedback to those people."
 
Chris and Denise maintained tight alignment at the top level of their organizations through four CEO transitions. Their partnership created a culture of accountability that cascaded through both teams. When either hired senior people who didn't fit the culture, they investigated and addressed it. The coaching approach wasn't about winning by authority—it was about maintaining partnership and shared accountability for results. This required unlearning traditional management approaches that pit departments against each other and instead fostering genuine collaboration.
Cultural Behaviors That Scale (And Those That Don't)
"We got dumb and lazy. We forgot about it. And then we decided, hey, we're gonna go get a little bit more fit, and figure out how to go get the new logos again."
 
Chris describes himself as a "velocity salesperson" with a hyper-focus on new customer acquisition. This focus worked brilliantly during Snowflake's growth phase—land customers, and the high net retention rate would drive expansion. However, as Snowflake prepared to go public, they took their foot off the gas on new logo acquisition, believing not all new logos were equal. This turned out to be a mistake. In his final year at Snowflake, working with CEO Sridhar Ramaswamy, they redesigned the sales team to reinvigorate the new logo acquisition machine. The lesson: the cultural behaviors that fuel early success must be consciously maintained and sometimes redesigned as you scale.
Keeping the Message Narrow Before Going Platform
"Eventually, I know you want to be a platform. But having a targeted market when you're initially launching the company, that people are spending money on, makes it easier for your sales team."
 
Snowflake intentionally positioned itself in the enterprise data warehousing market—a $10-12 billion annual market with 5,000-7,000 enterprise customers—rather than trying to sound "bigger" as a platform play. The strategic advantage was accessing existing budgets. When selling to large enterprises that go through annual planning processes, fitting into an existing budget means sales cycles of 3-6 months instead of 9-18 months. Yes, competition eventually tried to corner Snowflake as "just a cute data warehouse," but by then they had captured significant market share and could stretch their wings into the broader data cloud opportunity.
Selling Consumption-Based Products to Fixed-Budget Buyers
"Don't believe anything I say, try it."
 
One of Snowflake's hardest challenges was explaining their elastic, consumption-based architecture to procurement and legal teams accustomed to fixed budgets. In 2013-2015, many CIOs still believed data would stay in their data centers. Snowflake's model—where customers could spin up a thousand servers for 4 hours, load data, while analysts ran queries without performance impact—seemed impossible. Chris's approach was simple: set up proof of concepts and pilots. Let the technology speak for itself. The shift from fixed resources to elastic architecture required changing not just technology but entire mindsets about how data infrastructure could work.
 
About Chris Degnan
Chris Degnan is a builder of one of the most iconic revenue engines in enterprise software. As the first sales hire at Snowflake, he helped scale the company from zero customers to billions in revenue. Chris co-authored Make It Snow: From Zero to Billions with Denise Persson, documenting their journey of building Snowflake's go-to-market organization. Today, Chris advises early-stage startups on building their go-to-market strategies and works with Iconiq Capital, the venture firm that led Snowflake's Series D round.
 
You can link with Chris Degnan on LinkedIn and learn more about the book at MakeItSnowBook.com.

Prabhleen Kaur: The Art of Coaching Product Owners on What vs. How
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
The Great Product Owner: Master of Stakeholder Relationships and the Power of No
"The best PO is the person who has the superpower of saying no, and they can deal with the stakeholders with the same prowess." - Prabhleen Kaur
 
Prabhleen describes working with a Product Owner who managed multiple stakeholders—not just a handful, but a significant number with competing priorities. What made him exceptional was his deep understanding of each stakeholder's pulse and motivations. He knew when to push back and how to frame the "no" in a way that stakeholders could accept. This wasn't random resistance—it came from thorough preparation manifested in clear roadmaps that made most incoming work predictable for the team. 
His user stories stood out for their richness in context: beyond the business requirements, they included information about who would be impacted, which proved invaluable for a team dealing with multiple interconnected systems. 
He leveraged JIRA's priority field effectively, ensuring the moment anyone opened the board, they could immediately understand what mattered most. Prabhleen emphasizes that this PO understood his role as the "what" while respecting the team as the "how." By maintaining strong stakeholder relationships built on mutual understanding, he created space for the team to prepare, plan, and deliver without constant firefighting.
 
Self-reflection Question: Does your Product Owner have the preparation and stakeholder relationships needed to confidently say "no" when priorities compete, or does every request become an emergency?
The Bad Product Owner: Technical Experts Who Manage the Sprint Backlog
"The PO is the what, and the team is the how. When POs start directing the team about how to do things, the sprint goal gets compromised." - Prabhleen Kaur
 
Prabhleen addresses a common anti-pattern she's observed repeatedly: Product Owners with technical backgrounds who cross the line from "what" into "how." When POs come from developer or technical roles, their expertise can become a liability if they start prescribing solutions rather than defining problems. 
They direct the team on implementation approaches, suggest specific technical solutions in user stories, and effectively manage the sprint backlog instead of focusing on the product backlog. The consequences are predictable: stories keep getting added or removed mid-sprint, the sprint goal becomes meaningless, and the team ends up delivering nothing because focus is constantly shifting. 
Prabhleen's solution starts in backlog refinement, where she ensures conversations about technical approaches happen openly with the whole team during estimation. When a PO suggests a specific implementation, she facilitates discussion about alternatives, allowing the team to voice their perspective. 
The key insight: everyone comes from a good place—the PO suggests solutions because they believe they're helping. The Scrum Master's role is to create space for the team to own the "how" while helping the PO see the value in stepping back.
 
Self-reflection Question: When your Product Owner has technical expertise, how do you help them contribute their knowledge without directing the team's implementation choices?
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
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About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: When Team Members Raise Concerns with Clarity, Not Anger
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"My idea of success as a Scrum Master is when you look around, you see motivated people, and when something goes wrong, they come to you not in anger, but with concern." - Prabhleen Kaur
 
Prabhleen offers a refreshing perspective on measuring success as a Scrum Master that goes beyond velocity charts and feature counts. She shares a pivotal moment when her team was in production, delivering relentlessly with barely any time to breathe. A team member approached her—not with frustration or blame—but with thoughtful concern: "This is not going to work out." He sat down with Prabhleen and the Product Owner, explaining that as the middle layer in an API creation team, delays from upstream were creating a cascading problem. 
What struck Prabhleen wasn't just the identification of the issue, but how he approached it: with options to discuss, not demands to make. This moment crystallized her definition of success. When team members feel safe enough to voice concerns early, when they come with ideas rather than accusations, when they see themselves as part of the solution rather than victims of circumstances—that's when a Scrum Master has truly succeeded. 
Prabhleen reminds us that while stakeholders may focus on features delivered, Scrum Masters should watch how well the team responds to change. That adaptability, rooted in psychological safety and mutual trust, is the true measure of a team's maturity.
 
Self-reflection Question: When problems emerge in your team, do people approach you with defensive anger or constructive concern? What does that tell you about the psychological safety you've helped create?
Featured Retrospective Format for the Week: Keep-Stop-Happy-Gratitude
Prabhleen shares her favorite retrospective format, born from necessity when she joined an established team with dismal participation in their standard three-column retrospectives. She transformed it into a four-column approach: (1) What should we keep doing, (2) What should we stop doing, (3) One thing that will make you happy, and (4) Gratitude for the team. The third column—asking what would make team members happy—opened unexpected doors. Suggestions ranged from team outings to skipping Friday stand-ups, giving Prabhleen real-time insights into team needs without waiting for formal working agreement sessions. The gratitude column proved even more powerful. "Appreciation brings a space where trust is automatically built. When every 15 days you're sitting with the team making a point to say thank you to each other for all the work you've done, everybody feels mutually respected," Prabhleen explains. This ties directly to the trust-building discussed in Tuesday's episode—using retrospectives not just to improve processes, but to strengthen the human connections that make teams resilient.
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
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About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: How AI Is Changing the Way Agile Teams Deliver Value
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"AI's output is not the final output—it's always the two eyes we have that will get us the best results." - Prabhleen Kaur
 
Prabhleen brings a timely challenge to the coaching conversation: the impact of AI on teams and how Scrum Masters should navigate this transformation. She frames it as both a challenge and an opportunity—teams are now capable of delivering faster than consumers can absorb, fundamentally changing expectations and dynamics. 
Prabhleen has observed her teams evolve from uncertainty about AI to confidently leveraging it for practical benefits. Developers use AI for writing and understanding code, particularly helpful for onboarding new team members who need to comprehend existing codebases quickly. QA professionals find AI invaluable for generating test cases based on story and epic context already captured in JIRA. 
The next frontier? Agentic AI, where AI systems communicate with each other to produce better outputs. But Prabhleen offers an important caution: AI is learning from many conversations, not all of which are reliable. The human element—critical thinking and verification—remains essential. 
For Scrum Masters, this means facilitating conversations about how teams want to experiment with AI, exploring edge cases in testing that AI can help identify, and helping teams navigate the evolving landscape of possibilities while maintaining quality and judgment.
 
Self-reflection Question: How are you helping your team explore AI as a tool for improvement while ensuring they maintain critical thinking about the outputs AI produces?
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
[The Scrum Master Toolbox Podcast Recommends]
 
About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.

Prabhleen Kaur: When Lack of Trust Turns Teams Into Isolated Individuals
Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.
 
"Teams self-destruct despite best efforts when they lack trust." - Prabhleen Kaur
 
Prabhleen observed a troubling pattern while shadowing a team: stand-ups had become a register activity where people reported individual status without any connection to the sprint goal. There was no "we" in the conversation—only "I." 
The team had experienced a missed deadline due to a PR conflict that wasn't merged in time, but instead of addressing it openly, everyone focused on fixing the immediate problem while avoiding the deeper conversation. The discomfort was never voiced, and resentment accumulated silently. 
Prabhleen explains that team destruction is never about one action—it's about the accumulation of unspoken concerns that eventually explode at the worst possible moment. To rebuild trust, she recommends starting with peer reviews that encourage natural collaboration and conversation. 
Scrum Masters must be vocal about challenges in front of the entire team, modeling the openness they want to see. For teams that have completely withdrawn, anonymous feedback and scheduled one-on-ones can create safe spaces for honest communication. The key insight? Trust is rebuilt when people realize they will be heard and understood, not judged.
 
In this segment, we talk about how trust is the foundation of effective teams and how its absence leads to working in silos.
 
Self-reflection Question: When your team experiences a failure or missed deadline, do you create space for open conversation about what happened, or does everyone quietly move on while resentment builds?
Featured Book of the Week: Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland
Prabhleen recommends Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland as a foundational read for understanding the spirit behind the framework. "When I actually read the book and understood the nuances of rugby and how the team should be, everything started making sense. I grew beyond the Scrum guide, beyond following rules—it's about how the team operates around you as a collective," she explains. Prabhleen also highly recommends Turn the Ship Around by David Marquet, summarizing its core message as "leaders lead leaders." Both books shaped her understanding that frameworks exist to enable collaboration, not to create compliance. Check out the David Marquet episodes on the Scrum Master Toolbox Podcast for more insights on intent-based leadership.
 
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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥
Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.
 
🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.
 
Buy Now on Amazon
 
[The Scrum Master Toolbox Podcast Recommends]
 
About Prabhleen Kaur
 
Prabhleen is a Certified Scrum Master with 7+ years of experience helping teams succeed with SAFe, Scrum and Kanban. Passionate about clean backlogs, powerful metrics, and dashboards that actually mean something. She is also known for making JIRA behave, driving Agile transformations, and helping teams ship value consistently and confidently.
 
You can link with Prabhleen Kaur on LinkedIn.