Every SaaS has to Find Product Market Fit again -- ClickUp's COO on AI and Growth - 1MA S02E02

Every SaaS has to Find Product Market Fit again -- ClickUp's COO on AI and Growth - 1MA S02E02

In this episode of the One Message Away Podcast, host Andrej Persolja sits down with Gaurav Agarwal, the driving force behind ClickUp’s explosive growth and a leading voice in GTM and AI transformation. Dive into an in-depth discussion about scaling companies using PLG (Product-Led Growth) plus SLG (Sales-Led Growth) models, and why the old debates about choosing one motion over another are outdated in today’s AI-powered world. Listen as Gaurav Agarwal shares real-world leadership lessons from scaling a $300M+ business, building a culture of extreme ownership and accountability, and assembling high-performance teams at lightning speed. The conversation goes deep on: - The challenges and breakthroughs of blending PLG + SLG - How AI is fundamentally reshaping GTM, marketing, and operational excellence - The transition from being an “operator” to a “shareholder mindset” leader - What it takes to hire and motivate high-ownership, passionate teams in the age of AI - The future of work: orchestration of agents, and what it means to be an “E-shaped” marketer - How ClickUp is staying ahead as an AI-native system of work (and the unique competitive moat that creates) - Practical tips for leaders on measuring real output, finding business-market fit, and embracing relentless innovation Whether you’re a founder, marketer, product leader, or just curious about the future of AI at work—this conversation is packed with hard-won insights and actionable takeaways. Timestamps and key highlights available in video chapters. 00:00 PLG vs SLG vs... 03:56 Measuring True Value Drivers 08:30 Aligning Purpose for Motivation 12:05 How to get ahead in your career 16:37 What ClickUp looks for in a hire 18:46 ClickUp's Growth Breakthroughs 22:44 AI-Driven Marketing Transformation 27:40 The speed of testing in AI 31:28 What to vibe code and what to buy? 38:47 Marketer's role in the age of AI 40:37 Future Belongs to E-Shaped Thinkers 44:57 ClickUp's Unique Productivity Moat Like, comment, and subscribe for more brilliant minds shaping the future of work and AI! — Connect with Gaurav Agarwal: LinkedIn (search "Gaurav Agarwal ClickUp") Listen to more episodes of the One Message Away Podcast! #PLG #SLG #AI #ClickUp #Productivity #GTM #Leadership #SystemsThinking

1 Message Away 2x01 Know your numbers with Yann Skaalen

Welcome to another episode of the One Message Away Podcast! Today, host Andrej Persolja sits down with data expert Yann Skaalen to unravel the challenges SaaS founders, CEOs, and marketers face with tracking, attribution, and ad spend in an increasingly complex digital landscape. Episode Highlights: * Why founders drown in wrong data, not a lack of it * How GDPR and iOS updates have made accurate tracking more difficult * Double-reporting and attribution windows: Google vs. Meta – which numbers can you trust? * The shocking truth about wasted ad spend—sometimes up to 93%! * Server-side tracking and compliance: What makes DigTective’s approach unique * AI’s growing role in marketing analytics and decision-making * Real-world case studies and actionable strategies to optimize your ad budget * The importance of feeding accurate numbers to your AI models * In-house vs. agency vs. freelancer: Who should manage your ads? * Must-read resource: April Dunford’s game-changing book on positioning Whether you’re scaling a SaaS startup or simply want to cut through the marketing analytics noise, this episode is packed with practical wisdom and stats you won’t hear anywhere else. Connect with Yann: https://www.linkedin.com/in/skaalen/ Learn about DigTective’s 100% accurate approach at https://digtective.com Recommended Reading: April Dunford – "Obviously Awesome" (A favorite for both speakers!) If you enjoyed this episode, don’t forget to like, subscribe, and share! Drop your questions or thoughts in the comments—you might just get featured in the next episode. 00:00 Marketing Growth Analysis Challenges 05:30 Budget Challenges and Data Accuracy 07:11 "GDPR-Compliant Conversion Tracking" 10:27 "Challenges in Data-Driven Marketing" 15:13 Uncertainty in Tracking Systems 17:09 "Old-School Marketing Insights" 20:17 AI Revolutionizing Ad Targeting 26:01 SaaS Marketing Budget Mismanagement 26:45 "Lost Profitable Campaigns" 32:06 Growth-Driven Investment and Tracking Challenges 34:28 "Trust Numbers in AI Era" 38:31 AI Transforms Financial News Analysis 40:14 "Jacob's Game-Changing AI Tools" 43:37 "Favorite Nonfiction Book's Impact"

S01E08 - Stand out in crowded markets: Becoming a Niche Leader

* Test your Positioning Authority and get a benchmark score against the industry: https://apersolja.com/positioning-authority-assessment-tool/ [https://apersolja.com/positioning-authority-assessment-tool/] * The waitlist for the 90-day plan to become a niche leader is now open: JOIN [https://1messageaway.com/?p=1345#link-popup] (or here if link doesn’t work [https://one-message-away.kit.com/3e41a59978]) * Have your say for season 2: SURVEY [https://form.jotform.com/andrej.persolja/Survey] Welcome to the final episode of the first season of the One Message Away Podcast! In this special episode, host Andrej Persolja dives deep into his comprehensive approach to differentiation, helping you stand out in crowded markets and become a niche leader in your industry. Throughout the season, we've explored the essential elements of differentiation, emphasizing that it's not about being the loudest but about resonating best with your ideal customers. Andrej recaps our journey and reveals his three-step process for achieving effective differentiation. In this episode, you'll discover: * Why positioning misalignment can be a company killer and how to test for it. * An exercise to ensure your team is aligned on your company's goals and product focus. * Insights into conducting a positioning audit and building a growth team. * Strategies for uncovering market data through surveys, interviews, and focus groups. * How to develop and test three different positioning strategies to find the right fit for your company. Whether you're struggling with high user acquisition costs, low conversion rates, or simply want to scale effectively, this episode is packed with actionable insights to help you succeed. If you want to learn more and receive a 90-day plan on positioning your company as a niche leader, participate in our survey linked in the description. Your feedback will also help shape the content for season two! Thank you for joining us this season. Don't forget to like, subscribe, and hit the notification bell to stay updated with our new content. Subscribe to our newsletter for more in-depth insights and strategies. May your customers love you and truly understand your products! #Differentiation #Positioning #NicheLeadership #BusinessStrategy #MarketPositioning #Podcast SOCIALS * Connect on LinkedIn: https://www.linkedin.com/in/apersolja/ [https://www.linkedin.com/in/apersolja/] * Follow on Threads: https://www.threads.net/@apersolja [https://www.threads.net/@apersolja] NEW * Follow on IG: https://www.instagram.com/apersolja/ [https://www.instagram.com/apersolja/]  * Follow on Bluesky: https://bsky.app/profile/apersolja.bsky.social [https://bsky.app/profile/apersolja.bsky.social] NEW KEYWORDS content strategy, thought leadership, authority building, AI company, leads, content challenges, strategy duration, client understanding, resonating content, content experimentation, content consistency, content promotion, LinkedIn content, top of funnel content, short form content, podcasts, long form videos, blogs, case studies, sales process, positioning problem, authority positioning, personal profiles, management exposure, content analysis, company page growth, lead engagement, personalized content, systematic approach, competitive advantage BIO Andrej Persolja is a visionary positioning strategist known for his candid perspective on the challenges faced by modern companies. With a keen understanding of the saturated markets and the struggle for differentiation, Andrej has built his career on helping companies discover their unique essence. His insights into the mundanity that often plagues organizations have positioned him as a thought leader, inspiring businesses to break free from the monotony and find their distinct voice in a crowded world. Through his innovative approaches, Andrej helps companies uncover what truly makes them special, navigating them towards a path of genuine distinction and success. TIMESTAMPS 00:00 Effective Website Positioning Strategy 04:49 Aligning Departmental Focus Questions 06:52 Company Growth: Key Strategy Questions 13:03 Future-Proofing Business Strategy 16:01 Identify and Align Company Focus

S01E07 - Leading with content

* Test your Positioning Authority and get a benchmark score against the industry: https://apersolja.com/positioning-authority-assessment-tool/ [https://apersolja.com/positioning-authority-assessment-tool/] * The waitlist for the 90-day plan to become a niche leader is now open: JOIN [https://1messageaway.com/?p=1345#link-popup] (or here if link doesn’t work [https://one-message-away.kit.com/3e41a59978]) * Have your say for season 2: SURVEY [https://form.jotform.com/andrej.persolja/Survey] Welcome to Episode 7 of the One Message Away from the Nail Your Positioning Podcast hosted by Andrej Persolja! In this episode, we're diving deep into the world of content strategies and identifying where many go wrong. Join us as Andrej breaks down the five biggest reasons why content strategies fail and how you can avoid these pitfalls. From sticking to your strategy long enough to experimentation and consistency, Andrej offers valuable insights that can transform your approach to content creation. We'll cover: * The importance of giving your strategy time to produce results. * How to ensure your content resonates with your target audience. * The value of experimentation and testing to find what truly works. * Maintaining consistency in your message and topics. * How to effectively promote your products within your content. Andrej also shares real-world examples from his experience, including how he helped a growing AI company achieve remarkable results. You'll learn about the importance of short-form content for building leads and the role of middle and bottom funnel content in converting prospects into loyal customers. Whether you're in B2B, B2C, or leading a founder-led movement, this episode provides actionable strategies to enhance your content game. If you're ready to position yourself as an authority in your field, hit play and let's get started. Don't forget to like, subscribe, and click on all the links for exclusive bonus content and a chance to get your hands on the 90-day plan to position your company as a niche leader. SOCIALS * Connect on LinkedIn: https://www.linkedin.com/in/apersolja/ [https://www.linkedin.com/in/apersolja/] * Follow on Threads: https://www.threads.net/@apersolja [https://www.threads.net/@apersolja] NEW * Follow on IG: https://www.instagram.com/apersolja/ [https://www.instagram.com/apersolja/]  * Follow on Bluesky: https://bsky.app/profile/apersolja.bsky.social [https://bsky.app/profile/apersolja.bsky.social] NEW KEYWORDS content strategy, thought leadership, authority building, AI company, leads, content challenges, strategy duration, client understanding, resonating content, content experimentation, content consistency, content promotion, LinkedIn content, top of funnel content, short form content, podcasts, long form videos, blogs, case studies, sales process, positioning problem, authority positioning, personal profiles, management exposure, content analysis, company page growth, lead engagement, personalized content, systematic approach, competitive advantage BIO Andrej Persolja is a visionary positioning strategist known for his candid perspective on the challenges faced by modern companies. With a keen understanding of the saturated markets and the struggle for differentiation, Andrej has built his career on helping companies discover their unique essence. His insights into the mundanity that often plagues organizations have positioned him as a thought leader, inspiring businesses to break free from the monotony and find their distinct voice in a crowded world. Through his innovative approaches, Andrej helps companies uncover what truly makes them special, navigating them towards a path of genuine distinction and success. TIMESTAMPS 00:00 "Mastering Content for Long-Term Success" 03:28 Experiment More with Content 09:15 Boost Leads with Short-Form Content 12:19 Positioning as Authority in Sales 15:56 Monthly Content Strategy & Feedback 18:05 Streamlining B2B Marketing Funnel 20:57 "Subscribe for Exclusive Content"

S01E06 - From Sales-led to Product-led

* Test your Positioning Authority and get a benchmark score against the industry: https://apersolja.com/positioning-authority-assessment-tool/ [https://apersolja.com/positioning-authority-assessment-tool/] * The waitlist for the 90-day plan to become a niche leader is now open: JOIN [https://1messageaway.com/?p=1345#link-popup] (or here if link doesn’t work [https://one-message-away.kit.com/3e41a59978]) * Have your say for season 2: SURVEY [https://form.jotform.com/andrej.persolja/Survey] In episode 6 of the One Message Away Podcast, host Andrej Persolja dives deep into the complexities of choosing the right business model in today's unpredictable market. As SaaS sales decline and the corporate world grows cautious of startup collaborations, businesses must evaluate whether to pivot from a sales-first approach to product-led growth, or vice versa. Andrej discusses key indicators for when it's time to innovate your business model, challenges of making the shift, and the critical role of team dynamics in this transformation. With insights from working with over 300 companies, Andrej explores the costs, time, and strategic shifts necessary for a successful transition, drawing from real-world examples and his extensive experience. Tune in to discover how to stand out in a saturated market and gain an unfair advantage through the right business strategy. Whether you're focused on becoming a niche leader or optimizing your current model, this episode provides valuable guidance for navigating business model changes. Listen now and make sure to like, subscribe, and join the waiting list for Andrej's free 90-day plan to become a niche leader! #BusinessModelInnovation #ProductLedGrowth #SalesStrategy #BusinessStrategy #SaaS #Entrepreneurship #NicheMarket #AndrejPersolja #NailYourPositioningPodcast SOCIALS * Connect on LinkedIn: https://www.linkedin.com/in/apersolja/ [https://www.linkedin.com/in/apersolja/] * Follow on Threads: https://www.threads.net/@apersolja [https://www.threads.net/@apersolja] NEW * Follow on IG: https://www.instagram.com/apersolja/ [https://www.instagram.com/apersolja/]  * Follow on Bluesky: https://bsky.app/profile/apersolja.bsky.social [https://bsky.app/profile/apersolja.bsky.social] NEW KEYWORDS Product growth, SaaS sales, enterprise sales, business model, pivot business model, marketing problems, niche leader, saturated market, technology improvements, product development, resources, price competition, lead generation, sales cycles, market volatility, cash flow, startups, product led growth, sales enterprise, funnel, product market fit, product marketing, appointment setter, growth marketers, digital funnels, lead magnets, PLG, corporate bank sales, AppSumo, lifetime deals, investment strategy BIO Andrej Persolja is a visionary positioning strategist known for his candid perspective on the challenges faced by modern companies. With a keen understanding of the saturated markets and the struggle for differentiation, Andrej has built his career on helping companies discover their unique essence. His insights into the mundanity that often plagues organizations have positioned him as a thought leader, inspiring businesses to break free from the monotony and find their distinct voice in a crowded world. Through his innovative approaches, Andrej helps companies uncover what truly makes them special, navigating them towards a path of genuine distinction and success. TIMESTAMPS 00:00 Choosing the Right Business Model 06:19 Challenges of Niching and Sales Timing 09:55 Switching to Product-Led Growth Challenges 12:33 Engineering Firm's Shift to PLG Strategy 15:41 "Transitioning to Product-Led Growth" 17:53 Align Team Goals for Growth