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Pooja tries to convince Gurdeep to open up a shared bank account, plus Gurdeep tells you why you NEVER leave a game early ...AND... Pooja small-talks Channing Tatum on the red carpet!
Pooja and Gurdeep spill some never before heard stories of celebrity interactions through their 20+ years in the biz, plus Gurdeep's side-hustle as a fledgling actor ...AND... celebrity photographer George Pimintel brings us the hot 'goss' from the red carpet!
#280 Strategy | In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation.Dave and Gurdeep cover:The role of Demand Gen in 2025 (and what's changed)Why Brand and Reputation should be prioritized over Lead GenerationProven strategies to create urgency and close sales deals in enterprise marketsA glimpse into ContentStack's team structure and how they plan for growthTimestamps(00:00) - - Intro to Gurdeep (06:51) - - Brand and Audience Marketing (08:03) - - How the Role of Demand Gen is Changing (12:13) - - Brand and Reputation > Lead Generation (17:03) - - How Contentstack is Doing Demand Gen (19:41) - - How to Create Urgency to Win Sales Deals (21:22) - - Making a Good Offer in B2B Marketing (22:38) - - Why Being Bold and Taking Risks is Important in Marketing (28:57) - - Selling Your Vision to Leadership (31:38) - - How Contentstack Has Over 10,000 Global ICP Accounts (36:21) - - Team Structure at Contentstack (41:19) - - Running Marketing and Operating a High-Performing Team (43:35) - - Setting Effective Annual Plans (45:50) - - AI's Role in Marketing (49:24) - - Closing Thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5
Sia & Bodhi start school, plus Pooja and Gurdeep reveal their first jobs ...AND... can you solve this viral riddle that MIGHT make your brain hurt?!?
Gurdeep shares his Uber pet peeve, plus Pooja does something for the first time ...AND... Gurdeep's nephew is in a band!
It's Back To School and Gurdeep gets his hands on Pooja's old report cards, plus Pooja's pep-talk becomes a roast ...AND... Gurdeep does 24 hours in New York with the help of Chat-GPT!
P&G share their favourite hilarious audio drops from the show, plus Gurdeep tries something new ...AND... would YOU bring your mom on a first date?
Gurdeep's back from vacation and tells you what he did with his week off ...AND... Pooja welcomes him back by asking the audience for advice on his love life.
The Net Promoter System Podcast – Customer Experience Insights from Loyalty Leaders
Episode 254: What if the future of AI in customer experience is built not by giant platforms but by small, reusable, open source AI agents? Gurdeep Pall, President of AI Strategy at Qualtrics, believes open, modular AI agents will outmaneuver big tech's locked-down systems. In this conversation from the X4 Summit, Gurdeep argues that “experience agents”—task-specific bots that can plug into any stack—will give companies more control, better performance, and real freedom. Closed AI platforms promise convenience, but they trap businesses in rigid walled gardens. Gurdeep argues that modular architectures unlock something better: flexibility, reuse, and evolution. “Break down the agents to very specific functionality,” he says. “And those agents can be invoked by many different agents for different types of tasks.” This isn't just a tech choice. It's a business and philosophical stance. Qualtrics is partnering with LangChain and releasing open connectors to build an ecosystem of interoperable agents. The goal? Let companies mix, match, and scale customer-facing systems without depending on any one vendor. “This is one semantic level up,” he says, comparing today's agentic architectures to the launch of the web and mobile eras. “What agents are going to do for user experience—taking our digital game to the next level—is very exciting.” Guest: Gurdeep Pall, President of AI Strategy, Qualtrics Host: Rob Markey, Partner, Bain & Company Give Us Feedback: https://bit.ly/CCPodcastFeedback Time-Stamped Topics: (00:01) Why Qualtrics is going all-in on open agentic AI (00:04) An overview of the Qualtrics and LangChain partnership (00:06) The modular architecture of “experience agents” (00:08) Why one task might require seven agents (00:09) How specialization allows reuse and scale (00:10) Rejecting the walled garden model (00:11) Making open systems friction-free (00:12) A real-time use case from the X4 stage (00:14) Plug and play simplicity for complex integrations (00:15) Why this is a new digital paradigm Time-Stamped Quotes: [7:00] “It's about how you break up the task. Like, when you call the human, the human didn't sit there and not do anything and the password got reset. The human went to a piece of software and they went and worked on it. So, what we are talking about here is the combination of software and the human, now organized most efficiently.” [8:00] “ If you're able to break down the agents to very specific functionality, then those agents can be invoked by many different agents for different types of tasks.” [10:00] “ There is one example of a very small, open system called the Internet, which somehow, through open standards, became one of the most incredible innovations of human beings ever. So what we are trying to do is to take a stand and say, 'We believe in open systems and we want to let our customers know that this is a choice.'”
Pooja has some thoughts on Gurdeep being on vacation, plus the gang talk vinyl ...AND... we find out why we should all consider drinking wine from a box!Reminder- there is a special keyword embedded in today's episode where you can win a $500 gift card to Shoppers Drug Mart. Simply text the keyword plus your full name to 981-981. Standard message rates apply. Go to www.seekyoursounds.com/contests for contest rules. The Top Picks Event is back at Shoppers Drug Mart. Shop the products that get all the likes and get PC Optimum points on participating products! Restrictions apply. Offers valid until September 5th, 2025 . Plus, open your PC Optimum app today to get more offers!
Gurdeep gets life advice from a future version of himself, plus Pooja almost misses the start of the show ...AND... the gang are shocked by this one thing YOU do in the shower.
Pooja and Gurdeep debate the ‘thank you' driving hand, plus Gurdeep reveals the thing he was told as a kid to get him to behave ...AND... while Pooja shares the same for Sia & Bodhi.
Pooja frets over Pasta Salad-Gate, plus we learn what your egg preference says about you ...AND... Gurdeep reveals how he sweet-talked his way into an internship.
Is it ok to have a gift registry for your divorce party, plus Pooja wonders about the human version of pets ...AND... Gurdeep reviews Happy Gilmore 2.
This week, Gurdeep ponders some deep questions, such as: ‘Is it ok to ‘haha emoji' your own text?' ‘Is it wrong to leave a concert early?' ...AND... ‘Are motorcycles the most obnoxious invention of all time?'
Gurdeep hangs out with Paul (sans Pooja), plus Pooja makes Strawberry Pasta ...AND... the gang ponders whether they'd leave their partners for one million dollars.
Controversial topic alert: Should new pet parents be afforded a parental leave, Pooja hacks her commute and Gurdeep has a spiritual experience.
After heeding your advice, Gurdeep carefully breaks up with his dentist, plus Pooja explains how to order the perfect cup of coffee ...AND... the gang struggle with the latest Gen-Z slang.
Gurdeep contemplates breaking up with his dentist, plus Pooja wonders what qualifies as oversharing on social media ...AND... Gurdeep shares the story of the time he thought he was getting fired.
Gurdeep wants to hang out with Pooja outside of work. Pooja thinks they should have firm barriers. So, P&G go to see renowned therapist Roxanne Francis for Friendship Therapy.
Gurdeep performs a magic trick live on-air, find out if it works on you! Plus, do mosquitoes like a certain bloodtype? ...AND....the gang reveal they were ‘today years old' when they learned this...
Pooja's in toddler hell, plus Gurdeep rings in Summer by quizzing the room ...AND... we learn why you ALWAYS take off your smartwatch before entering a mosh pit.
Is it ok to use AI to write your wedding vows, plus Pooja shares six words (from Harvard) women should use on their dating profile to entice right swipes ...AND... Gurdeep counters with his own (made up) list.
Gurdeep gets into an awkward situation with his mom, plus Pooja wonders about dating deal-breakers ...AND... the gang share their latest Shower Thoughts!
With Fathers Day coming up, Gurdeep wonders if men like receiving flowers, plus Pooja explains Chair Butt ...AND... you share your Dad-isms!
How many of these 8 bad morning habits are you guilty of? Plus, Gurdeep gives you his Top-5 John Candy movies ...AND... we discover yet ANOTHER thing Pooja has never experienced.
Pooja has some bad luck while travelling, plus Gurdeep struggles with a repairman ...AND... the gang call Connor McDavid of the Edmonton Oilers to wish him good luck in the Stanley Cup Final.
Pooja struggles with modern fashion, plus Gurdeep's dog is more popular than him ...AND... Pooja's FaceTime fail with her kids.
Gurdeep reveals his long buried childhood nickname, plus Stef vs Stef and no one wins ...AND... YOU share all the things you think should be illegal, but aren't!
Gurdeep reveals something embarrassing he did on a first date, plus Pooja FINALLY wins a game ...AND... Gurdeep is back on crutches after an unlikely injury.
Gurdeep shares a possible cure for hair loss, plus Pooja makes things awkward at work ...AND... we call our $32,750 CHFI Music Jackpot WINNER!
Pooja offers up a ‘unique' cleaning hack, plus Gurdeep shares the scent he can't stand ...AND... the gang take your calls for the Nearly Impossible Question.
To celebrate their 200th episode, Pooja and Gurdeep get personal and share a couple of harrowing stories that involved each of them having to call the police in their private lives!
Pooja explains why we may be doing pasta wrong, plus Gurdeep makes a startling admission ...AND... an anonymous listener texts in with a spicy Dear P&G.
Sia turns the tables on Mama Pooja, plus we talk partner pet names ...AND... Gurdeep searches for optimism ahead of Game 5 for the Maple Leafs.
Pooja shares an emotional letter to her mother, plus Gurdeep wonders about being replaced by AI ...AND... Pooj & Stef go head-to-head in a Mom Quiz.
Frankie Flowers stops by to explain why he's stepping away from morning TV, plus Gurdeep gets an unexpected surprise ...AND... Pooja reveals the top voted song of all-time.
Pooja and Stef grill Gurdeep about the lengths he'd go to for his “Dream Girl,” plus it turns out kids don't need much to be happy ...AND... can you do better than us in our Famous 5's quiz?
Pooja tries to sell the gang on spirulina, plus Gurdeep takes the temperature of Leafs Nation ...AND... if you say ‘please' and ‘thank you' to AI, here's why you should stop.
Stef finally buys a ‘grounding mat' and has her review, plus Gurdeep's nephew does something surprising ...AND... Pooja pines for Gurdeep to lose $1,000.
When you fly, do you prefer to sit WITH or APART from your partner? Plus, Gurdeep has group chat anxiety ...AND... Pooja sways Paul on a surprising issue.
Gurdeep tries to explain his ASMR, plus Pooja shares the follies of abbreviating your texts ...AND... we go back in time to re-live our FIRST email address.
Do you ever wonder what your pets get up to when you're not home, plus Gurdeep shares his irrational Playoff superstition ...AND... Pooja tells you why spreadsheets could save your relationship.
Did you know dogs have their own love language, plus Gurdeep reveals his Playoff Survival Kit ...AND... Pooja experiments with a new tactic to bring her closer to her husband.
The gang investigate the widely accepted “5 second rule,” plus Gurdeep stresses about tax season ...AND... Pooja discovers a helpful analogy to help you through tough times.
Gurdeep goes to a Coffee Party for the first time, plus P&G make you feel better about your bad boss ...AND... Pooja wonders if she's TOO affectionate with her kids!
Stef (tries) to explain “Grounding Sheets” to P&G – but they're skeptical, plus Gurdeep finally caves on reality TV ...AND... did you hug your siblings as a kid?
Pooja commits an egregious marital act and we let YOU be the judge, plus Gurdeep explains TLDR ...AND... are receding hairlines sexy now?!
A divorce lawyer has a scorching hot take on WHY women are choosing to get divorced – and it's not why you think. Plus, Pooja plays quizmaster as Gurdeep puts up $1,000 of his own money in Can't Beat Gurdeep.
In this episode of the Fail Faster Podcast, Gurdeep Singh, a seasoned solution architect at Chubb with over 25 years in the technology sector, shares his fascinating journey from dismantling radios in his childhood to tackling large-scale modernization projects in financial services. Gurdeep discusses the complexities of legacy system transformation, navigating organizational resistance, and the power of aligning business and technology for impactful change. He also shares his insights on leveraging AI responsibly, building strong data foundations, and fostering collaboration across all levels of an organization. Packed with lessons learned from career-defining challenges and forward-looking strategies, this episode is a must-listen for anyone aiming to modernize systems while keeping people at the heart of innovation.