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 software. We’ll dive into how he got his first customers by cold calling and we’ll discuss how he grew his company by publishing articles and...

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 with me on LinkedIn and Twitter (links below).  Thank you for tuning in and supporting the podcast—I look forward to seeing you back here very...

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 importance of marketing to a CEO, how to align your company metrics, and why you should be wary of 'yes-men'. I weigh in on cross-company collaboration,...

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 cultivating a growth practice. We discuss finding the right problem to solve, the importance of experimentation, and why she hires curious people. I...

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 purchase products.” Rob co-founded Salsify in 2012 and has grown the company to over 740 employees serving a roster of high-profile clients. Salsify...

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 executive.  In this episode, Casey shares some of that knowledge with us as we discuss creating a culture that prioritizes learning from failure, the...

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 down some of the strategies that have helped vFairs win. We discuss hiring for hyper-growth, the power of word of mouth, and why delivering high-quality...

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, marketing leadership, and category creation and shares his expertise through regular appearances at events and on podcasts. In this episode, Kevan walks...

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 discuss customers hacking your product, how to scrutinize your metrics, and the benefits of implementing an outbound sales strategy earlier. I weigh in on...

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 employs more than 100 people. Before Catalyst, Mark spent 8 years at the sales execution platform Outreach where he led their sales team as VP and later Senior...

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 things in the short term and underestimate their value in the long term. I weigh in on the idea of 'culture eats strategy for breakfast', being your...

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 advocate of using behavioral psychology, tech, data, and creativity to find exciting, new approaches to business. In this episode, Brian breaks down six...

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 the market, and unpack the B2B message layers framework. You'll also hear input from Drift's David Cancel, Andreessen Horowitz's Andrew Chen, and author of...

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 $24M in revenue and had a team of 230 that migrated over to Seismic. Lessonly was used by 1,200 B2B customers. In this episode, Kyle breaks down six...

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 PandaDoc successfully, their decision to make part of their product free, and how balancing external opportunities with a strong internal culture helped...

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 the UK and India. This year Kovai.co's annual revenue has topped $10 million. In this episode, we discuss the benefits of true thought leadership,...

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 and dominated their niche, the benefits of building a community around your product, and why continually innovating to add value should be part of your...

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 discuss the massive opportunity Aircall saw in the market, how they got an early leg up on the competition by being specific about their ICP, and why...

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 transitioning to a non-founder CEO, how assessing your business honestly is essential, and the idea of competing against non-consumption. I share my thoughts on...

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 why scaling company culture is key to successful growth. I weigh in on innovating for customer value, why you should always be generous with your knowledge,...

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 company wrapped up a $25M funding round bringing their total amount raised to around $200M. In this episode, we discuss how FullStory repositioned early on when...

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 round, and in under four years has earned a billion dollar valuation. In this episode, we take a look at Seamless' decision to stay focused on their core...

This week on How to Win: Alexander Graf, co-founder and co-CEO of Spryker, an e-commerce platform for B2B and B2C enterprise marketplaces. Founded in Germany in 2014, Spryker raised $130M in Series C funding in 2020 and now sits at 650 global employees with 100% growth, year over year. In this episode, we look into how Spryker turned years and years of industry experience into a deep moat, and the strategy behind their investment in brand image. I share my thoughts on the importance of a...

This week on How to Win: Anand Sanwal, co-founder and CEO of Attentive, a business intelligence platform that enables organizations to make technology decisions faster and with more confidence. Launched in 2010, CB Insights is on track to hit $100M ARR this year, with over 400 employees and thousands of customers. In this episode, we unpack CB Insights' highly successful content strategy, and discuss why the ability to prioritize has been essential to their growth. I weigh in with my thoughts...

This week on How to Win: Brian Long, co-founder and CEO of Attentive, an SMS marketing solution. Since being founded in 2016, Attentive had grown to over 1300 employees and recently raised $470M in Series E funding with a total of $866M raised to date. In this episode, we discuss Attentive's vertical focus, obsession with customer feedback, and success with their outbound sales efforts. I share my thoughts on playing in market verticals, adjusting to a rapidly evolving competitive landscape,...