Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories. No fluff. No filler. Just strategies and tactics from founders, executives, and marketers. Learn about building moats, growing audiences, scaling businesses, and differentiating from the competition. New guests every week. Hosted by Peep Laja, founder at Wynter, Speero, CXL.
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Peep Laja dives into why speed is a critical and often underrated competitive advantage in today's fast-paced business world. Learn how to make swift decisions, conduct rapid experiments, ship products and campaigns quickly, and gather market feedback efficiently. Drawing from historical military strategies and modern business practices, Peep expla…
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In this episode, Peep Laja emphasizes the importance of deeply understanding your target market and ideal customer profile (ICP) to drive growth in B2B SaaS. He advocates for ongoing research to inform effective messaging, breaks down the key components of high-converting copy, and shares how tools like Wynter enable teams to get fast feedback and …
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In this episode, Peep dives into why niching down is the key to success for early-stage B2B SaaS companies. He explains how focusing on solving a specific problem for a targeted market, rather than competing directly with industry giants, allows startups to gain traction and dominate their niche. Peep emphasizes that niching down isn't about limiti…
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In this episode, Peep Laja explores the scientific laws of marketing, focusing on building mental and physical availability for brands. Drawing from the works of Professor Byron Sharpe and the Ehrenberg Bass Institute, Laja emphasizes the importance of being top of mind and easily found when potential customers are ready to make a purchase. The epi…
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This episode explores the critical factors that define market leadership, from being first in a category to leveraging innovation and strategic marketing. Hear from experts like David Aaker, Mark Ritson, and Byron Sharp on how top brands maintain dominance and why small brands face uphill battles. Discover actionable insights on standing out, stayi…
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In this new style of "How To Win", Peep Laja discusses the importance of differentiation in today's highly competitive B2B SaaS market. He explores various strategies for standing out, such as focusing on brand, taking a polarizing stance, being radically transparent, and leveraging personal brands. Laja emphasizes that differentiation is a CEO-lev…
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The Secret Sauce to $80M Bootstrapped - with AppSumo's Noah Kagan
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This week on How To Win: Noah Kagan of AppSumo, a platform for digital marketplace deals focusing on software aimed at entrepreneurs and small businesses. They have bootstrapped to over $80 million in revenue. You’ll hear insights on scaling business by focusing on what works, the importance of staying true to your core values, and the strategy beh…
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From Zero to Unicorn: Factorial HR's Strategic Success - with Factorial HR's Bernat Farrero
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This week on How To Win: Bernat Farrero of Factorial HR, sharing insights on revolutionizing HR for SMBs. You’ll hear about the importance of simplifying complex HR processes for small and medium businesses, Factorial HR's strategic approach to scaling internationally while addressing localized needs, and how they navigated the challenges of rapid …
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Scaling Beyond $100M and Creating New Categories - with Pendo's Todd Olson
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This week on How To Win: Todd Olson of Pendo, revealing the secrets behind building a product-led growth company. You’ll hear how Pendo's focus on product experience revolutionized customer interaction, the importance of integrating customer feedback into product development for sustained growth, and the strategic approach to scaling a software com…
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Building a $180M PR Powerhouse with MuckRack's Gregory Galant
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This week on How To Win: Gregory Galant of Muck Rack, discusses the journey of transforming a podcasting venture into a leading software solution for public relations professionals. You’ll hear insights on the importance of building strong journalist relationships, the strategic pivot from service to software, and the value of slow, deliberate grow…
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Disrupting the B2B Marketplace -- with TrustRadius's Vinay Bhagat
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This week on How To Win: Vinay Bhagat of TrustRadius, revolutionizing B2B software buying with in-depth user reviews. You’ll hear how TrustRadius overcame the challenge of creating a trusted review platform in a saturated market, the strategic decisions that led to successful monetization, and the importance of focusing on quality over quantity to …
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The Differentiation Advantage - with Retention.com's Adam Robinson
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This week on How To Win: Adam Robinson of Retention.com, an innovative leader in the email marketing space. You’ll hear about the journey of identifying a market gap and creating a differentiated product in a competitive environment, the importance of strategic focus on a specific target market, particularly in e-commerce, and the implementation of…
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Finding Your Focus - with Blackthorn's Chris Federspiel
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This week on How To Win: Chris Federspiel of Blackthorn.io, a company specializing in Salesforce integration and application development. You’ll hear about Blackthorn's strategic approach to the Salesforce ecosystem, the critical role of customer feedback in shaping their product development, and the journey of focusing their offerings to achieve s…
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Finding Your Ideal Customer Profile - with Keap's Clate Mask
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This week on How To Win: Clate Mask of Keap, marketing automation and CRM platform for small businesses. You'll hear how Keap found the right customers, why they combined software with services, and how Keap evolved its marketing over time. Key Points: 01:15 Building the initial product based on own business needs 03:00 Pivoting to serve small busi…
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Moving Upmarket for Growth - with Process Street's Vinay Patankar
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This week on How To Win: Vinay Patankar of Process Street, a workflow management software company. You'll hear why they didn't monetize for the first 2 years, how going upmarket increased retention and revenue, and why they focused the product on specific use cases. Key Points: 01:15 Identifying market need from personal frustration 03:00 Deciding …
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Building a $15M+ Community - with Pavilion's Sam Jacobs
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This week on How To Win: Sam Jacobs of Pavilion, who built a $15 million community learning business from scratch. You’ll hear how he leveraged LinkedIn for organic growth, the importance of creating sub-communities, and key mistakes he made after raising VC money that took the focus away from his core customers. Key moments: 00:50 - Describing wha…
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Bootstrapped to IPO - with Backblaze's Gleb Budman
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This week on How To Win: Gleb Budman of Backblaze, which offers affordable, easy cloud storage. You’ll hear how bootstrapping forced them to make efficient decisions, how focusing on underserved mid-market customers helped them compete with Amazon, and how building their own platform gave them a structural advantage. Timestamps: 01:45 Focusing on u…
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Raising Prices 50X - with indinero's Jess Mah
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This week on How To Win: Jess Mah of indinero, a fintech company providing automated bookkeeping and accounting services. You'll hear how she focused on high-paying niche verticals, pivoted to find product-market fit, and how she brought in an experienced CEO. Key Points: 01:45 Pivoting to a new customer segment willing to pay more 03:00 Combining …
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Getting the Timing Right - with Jellyfish's Andrew Lau
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This week on How To Win: Andrew Lau of Jellyfish, the engineering management platform. You'll hear how they validated the problem space, figured out product-market fit, and used founder-led sales to generate traction. Key Points: 2:03 - Getting first revenue with founder-led selling 4:12 - Seeing massive growth after increasing COVID demand 6:33 - …
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Landing Bigger Clients - with UserGems' Christian Kletzl
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Summary This week on How To Win: Christian Kletzl of UserGems, champion tracking software for sales. You'll hear the process they went through to find the product their clients were willing to pay for, how they make themselves appear bigger than they are, and more. Key Points 00:30 - Appearing larger by using ads, content, LinkedIn, conferences 01:…
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Growing a SaaS Under HEAVY Competition - with Livestorm's Gilles Bertaux
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This week on How To Win: Livestorm's Gilles Bertaux, a meeting and webinar platform. You'll hear how Livestorm succeeded despite many well-known competitors. How they got their first customers. And how they grew past $10 million in revenue. Key Points 1:00 - How Gilles got the idea for Livestorm and validated it with customers 2:00 - Getting the fi…
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Rebuilding the ICP - with Wonder's Guy Cohen
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This week on How To Win: Guy Cohen, CEO of Wonder an on-demand secondary research platform. They built the company to 8M in revenue, realized their ICP was wrong, tore it down and rebuilt again. That's what we break down in this episode. Key Points: 00:02:29 Failed many times, learned hard lessons, narrowed target. 00:04:28 Innovative marketing app…
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The Multi-Product Strategy - with Podia's Spencer Fry
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Summary This week on How To Win: Spencer Fry of Podia, the all-in-one platform for publishing, promoting, and selling content online. You'll learn how Podia succeeded in the face of heavy competition. Why the benefits of having multiple products outweigh the downsides for Podia. How Podia's long-term investment affects everything from product creat…
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Selling 1000s of SaaS Startups - with Acquire's Andrew Gazdecki
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Summary This week on How To Win: Andrew Gazdecki of Acquire.com, the startup acquisition marketplace. You'll hear: How Andrew lands Times Square advertising to promote startups on his platform. How he went from doing everything himself to quickly assembling a team to speed up his company's growth rate. How he discovered a big opportunity to create …
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Growing a SaaS by Launching a Service - with Boast AI’s Lloyed Lobo
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Summary This week on How To Win: Lloyed Lobo, founder of Boast AI, which helps companies find and claim tax credits from their R&D investments. LLoyed launched two different software companies, which failed. He followed it up with a service business, Boast, which took off. You’ll hear why he thinks services are a better way to launch a company than…
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With summer around the corner, How to Win will be taking a brief hiatus. During this time, the team will be working behind the scenes to bring you more exciting insights from today’s top B2B SaaS entrepreneurs and CEOs when we return in Fall 2023 with a brand new season. In the meantime, catch up on past episodes of How to Win, and stay connected w…
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Cross-company collaboration with Pluralsight's Lindsay Bayuk
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Summary: This week on How to Win: Lindsay Bayuk, CMO at Pluralsight, an online technology learning platform designed to help teams upskill. Pluralsight was founded in 2004 and was acquired by Vista Equity Partners in 2021. In this episode, Lindsay breaks down some of the strategies that have helped her as a CMO. We discuss communicating the importa…
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Cultivating a growth practice with Mural's Lauren Schuman
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Summary: This week on How to Win: Lauren Schuman, VP of Product Growth at Mural. Founded in 2011, Mural was valued at $2B after their Series C funding round in 2021. Before joining Mural, Lauren served as Senior Director of Product Insights and Growth at Mailchimp. In this episode, Lauren breaks down how she has steered Mural and Mailchimp toward c…
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Laying the foundation for long-term company alignment with Salsify's Rob Gonzalez
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Summary: This week on How To Win: Rob Gonzalez, co-founder and CMO of Salsify, a commerce experience management platform that helps its clients win on the 'digital shelf.' Salsify defines the digital shelf as: "The collection of diverse and rapidly evolving digital touch points used by shoppers to engage with brands and discover, research, and purc…
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Fostering a learning mindset in your company culture with Quantive's Casey Carey
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Summary: This week on How To Win: Casey Carey, CMO at Quantive and expert in B2B, e-commerce, and growth marketing. From heading up scaled marketing departments at giants like Google to helping build teams from the ground up at scrappy startups, Casey's expansive career has given him a wealth of knowledge and experience to draw on as a marketing ex…
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Creating a high-quality customer experience with vFairs' Muhammad Younas
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Summary: This week on How To Win: Muhammad Younas, CEO of vFairs, an all-in-one events platform that allows users to conduct virtual, in-person, and hybrid events. Founded in 2016, vFairs experienced accelerated growth during the pandemic and ballooned to over 250 employees with offices located around the world. In this episode, Muhammad breaks dow…
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Building a brand from the ground up with Oyster HR's Kevan Lee
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Summary: This week on How To Win: Kevan Lee, Senior VP of Marketing at Oyster HR, a management platform for globally distributed teams. Before joining Oyster, Kevan spent six years as VP of Marketing at Buffer, a social media management platform that helps brands and businesses engage with their online audience. Kevan is an expert in brand strategy…
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Reassessing your metrics with Earl Grey Capital's Matt Sornson
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Summary: This week on How To Win: Matt Sornson, co-founder of Clearbit. He spent seven years across multiple leadership roles at the company and now serves on the board. His new day job is being a partner at Earl Grey Capital, an early-stage venture fund. In this episode, Matt breaks down five key lessons he’s learned throughout his career. We disc…
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Five steps to grow your business with Catalyst Software's Mark Kosoglow
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Summary: This week on How To Win: Mark Kosoglow, B2B SaaS thought leader and CRO of the customer success platform Catalyst Software. Founded in 2017, Catalyst's founders saw a need to create a tool that integrated customer success tools into a platform that was easy to learn and implement. To date, Catalyst has raised over $45M in funding and emplo…
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Developing a long-term view with Userlytics Corporation's Alejandro Rivas-Micoud
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Summary: This week on How To Win: Alejandro Rivas-Micoud, Founder & CEO of Userlytics Corporation, a UX testing platform founded in 2009. In this episode, Alejandro breaks down six important lessons he’s learned throughout his career. We discuss creating a strong corporate culture, deciding not to use VCs, and why people overestimate the impact of …
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Identifying your company's leverage with SmartAsset's Brian Bourque
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Summary: This week on How To Win: Brian Bourque, SVP of Marketing at SmartAsset, where they've grown a lead generation business from $0 to $100M+ in revenue primarily through paid acquisition marketing and SEO. Brian has a ton of experience leading profitable paid acquisition teams in quantitative, direct-response marketing businesses. He's an advo…
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Getting inside your ideal customer's limited consideration set with Peep Laja
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Summary: This week on How To Win: I'm taking the opportunity to dive deeper into something we've touched on in previous episodes, but never given the complete attention it deserves: how to get inside the limited consideration set of your ideal customers. I'll share how to create mental availability beyond your product, how to position yourself in t…
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Six tips for building your business with Jellyfish's Kyle Lacy
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Summary: This week on How To Win: Kyle Lacy, Chief Marketing Officer at Jellyfish and former CMO at Lessonly, a sales training and coaching platform. Lessonly was acquired by Seismic in 2021. Kyle also served as the Director of Global Content Marketing at Salesforce after its acquisition of ExactTarget in 2014. Before its acquisition, Lessonly made…
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Feedback loops and free product offerings with PandaDoc's Mikita Mikado
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Summary: This week on How To Win: Mikita Mikado, CEO of PandaDoc. PandaDoc is an all-in-one document workflow automation platform. They launched in 2013, were valued at $1B in 2021, and have a projected revenue of $55M this year. They have 390 employees across the US and Belarus. In this episode, we discuss how they used customer feedback to pivot …
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Diversifying your product offering with Kovai.co's Saravana Kumar
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Summary: This week on How To Win: Saravana Kumar, CEO of Kovai.co, a software company offering multiple enterprise and B2B SaaS products including, a customer success product, a self-service knowledge base product, and enterprise software for Microsoft BizTalk and Azure Serverless platforms. Founded in, 2011, Kovai.co has over 240 employees across …
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Content, community, and customer acquisition with Mutiny's Jaleh Rezaei
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Summary: This week on How To Win: Jaleh Rezaei, CEO and co-Founder of Mutiny. Mutiny is a no-code AI and personalization platform for marketers. Mutiny launched in 2018, raised their Series A in 2021 with Sequoia Capital, and their Series B this year with Tiger Global. They now have over 70 employees. In this episode, we discuss how they carved out…
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Identifying the ICP with the greatest need with Aircall's Jonathan Anguelov
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Summary: This week on How to Win: Jonathan Anguelov, co-founder & CSO at Aircall, a cloud-based call center and phone system that seamlessly integrates with common productivity and help desk tools. Since its founding in 2014, Aircall has raised over $226M in funding and now sits at over $100M ARR with over 700 global employees. In this episode we d…
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Making the jump to a 'professional CEO' with Maxio's Randy Wootton
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Summary: This week on How to Win: Randy Wootton, CEO of Maxio, a platform offering subscription and revenue management solutions to SaaS companies. Founded in 2022, Maxio is the product of a merger between SaaSOptics and Chargify, brought together by private equity investment firm Battery Ventures. In this episode, we discuss the challenges of tran…
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Engineering the product mindset with 3Pillar Global's David DeWolf
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Summary: This week on How to Win: David DeWolf, President and CEO of 3Pillar Global, a software product development company. 3Pillar Global was founded in 2006 and now has over 2000 employees with annual revenue of over $100M. In this episode, we discuss going beyond a great product offering, why leaders should regularly reinvent themselves, and wh…
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Going after greenfield opportunities with FullStory's Scott Voigt
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Summary: This week on How to Win: Scott Voigt, founder and CEO of FullStory, a digital experience intelligence platform that combines quantitative and qualitative data to drive digital growth. Founded in Atlanta in 2014, FullStory now serves over 3200 customers and has consistently increased their ARR by over 70% year over year. In August, the comp…
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Focus-fueled growth with Seamless.AI's Brandon Bornancin
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Summary: This week on How to Win: Brandon Bornancin, founder and CEO of Seamless.AI, a platform focused on sales, lead generation, and prospecting via an advanced search engine. Launched in 2018, Seamless.AI grew out of a list-building agency called Seamless Contacts founded three years earlier. Seamless.AI recently completed a nearly $100M funding…
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Industry experience as a competitive advantage with Spryker's Alexander Graf
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Key Points: How Alexander and his co-founder got their start with Spryker (01:20) How Spryker adjusted to marketing to multiple decision makers after they passed the $1M ARR mark (05:06) My advice on managing your marketing while addressing a large stakeholder base, with a quote from Ismail Madni (08:21) Alexander discusses Spryker's different comp…
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Developing a distinctive marketing tone with CB Insights' Anand Sanwal
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Key Points: How CB Insights got its start (01:13) Anand explains when he realized the target market for CB Insights had shifted (03:33) My thoughts on the transient nature of the market, and why successful companies should be prepared to adapt with a quote from Bridgefy's Jorge Rios (05:03) Anand explains CB Insights' unique approach to content mar…
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Getting more accurate customer feedback with Attentive's Brian Long
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Key Points: How Brian got started with Attentive (01:04) My thoughts on the advantages of being vertical-specific with a quote from Steve Blank (02:52) Brian explains the competitive landscape Attentive was playing in at the start (04:23) Why selling should start with identifying the major problems facing your target customers (05:30) I discuss how…
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Winning in a large target market with Cognism's James Isilay
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Key Points: James explains how his trading background led him to founding Cognism (01:04) Cognism's first major pivot (02:25) My thoughts on early pivots with a quote from Eric Ries (03:39) James describes how Cognism's market size meant there was plenty of growth opportunity, despite competition (06:24) I explain the advantage of starting your bus…
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