The SaaS Revolution Show

On this month’s episode of the Struggle, Alex speaks with Yesware co-founder and chairman of the Board, Matthew Bellows. He interviewed him a year ago for another episode of the SaaS Revolution Show where the focus was on the part of the story that showcased Yesware’s success to date. Today they take a step back and, in the spirit of The Struggle,  chat about the myriad of struggles that Matthew has been through, that isn’t often discussed, on the way to that success. Matthew started Yesware in 2010 together with his co-founder and CTO Cashman Andrus. The plan was to bootstrap but as demand for engineering talent increased while savings were drying up very quickly, Matthew and Cashman decided to fundraise. According to the blog posts, they had read it was meant to be easy. The reality turned out anything but. While the experience was difficult, Matthew believes that for Yesware it was the right thing to do. It also served as an important gut check - Do we actually want to run this company and build this product? The answer was yes and eventually, they managed to raise a $1 million in 2011, which helped fuel the initial build of the communication platform for salespeople. Yesware has gone on to raise a total of $48 million. The Yes answer to that question has always remained. Matthew goes in-depth on why he never wanted to give up. He is incredibly open and honest throughout the conversation and covers a large array of topics such as the inherent conundrum of being CEO, how he has grappled with a very strong case of Imposter Syndrome, the struggles of managing executives, how meditation has helped him immensely, why he stepped down as a CEO in August last year and he feels about it. We finish off with the one piece of advice he would give to fellow founders and CEOs. This is the untold story of Yesware: 7 years in the making. If you would like to share your story of struggle with us on the show, get in touch by emailing podcast@saastock.com Listen to the original SaaS Revolution Show episode with Matthew Bellows You can find more information about his executive coach, Jerry Colonna here    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

On this episode of the show, we chat with Kieran Flanagan, VP Marketing at HubSpot, about the essentials of product qualified leads. A software engineer by education, Kieran very quickly figured out that he would be average at best when it came to building software products. Where he go excited was in getting people to use them, and grow that usage. Kieran’s path in figuring that out has seen him go through companies like Salesforce and Marketo, finally landing at HubSpot 6 years ago. Such a long tenure is unusual for people like Kieran who get easily bored but HubSpot has proved an incredibly interesting playground for experiments that he hasn’t been tempted to leave. In the past two years, he has been in charge of the entire top of the marketing funnel, which represents all the demand created through users and leads. A lot of that has been led by trials and use of freemium products. Listen on to hear: What is a product qualified lead How to know if a product-led strategy makes sense for your business How to begin transitioning to product qualified leads Kieran has spoken at three SaaStock conferences and will be back at SaaStock19, where we will bring many more marketers just like him. Sign up for our Insider sale to be the first to get access to our 2 for 1 ticket sale.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

On this bonus episode of the show, we bring you the keynote that Meghan Keaney Anderson, VP Marketing at HubSpot, gave at last year’s SaaStock on Tour in New York. Meghan goes in great detail on the year-long traffic plateau HubSpot’s blog went through in 2017 and how after the initial heart palpitations, the team upended the editorial strategy and are stronger than ever today. A creative writing major, Meghan joined HubSpot in 2011 when the growth graph of the blog looked like any content marketers dream - a hockey stick. That lasted for a few years until in 2017 it hit a plateau. In the first few months, Meghan and the team ascribed it to seasonality but as months went by with no changes they began to worry. As they would find out, many other companies were reporting similar results, and named that year, the great flattening of 2017. The journey to get out of the plateau began. Listen on to hear: Why were all companies seeing the plateau at that time? What was the first thing HubSpot did to accommodate to this new reality How did HubSpot optimize content to fit Google’s new algorithms To fully enjoy this podcast you can follow Meghan’s deck as you are listening. From June 4th to the 6th, we will be back in New York to run a bigger and better SaaStock East Coast conference featuring incredibly successful SaaS founders and executives such as Meghan, as well as key investors from the region. Find out more about SaaStock East Coast and buy tickets.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

On this week’s podcast, we talk with Cristina Vila, Founder of Cledara, which was crowned the Best SaaS Startup of 2018 during SaaStock18 in Dublin last year. Cristina grew up in Spain and from a young age enjoyed the dinner conversations with her dad, in which he would speak about running his business. The aptitude for entrepreneurship only increased from there, and on June 30th, 2018, Cristina left the startup she had been working for to start her own. The problem she had decided to solve was managing the abundance of SaaS products that companies were using. She had faced that very issue and upon failing to find a solution to help her, she decided to build one. Cristina raised a small angel round, employed the services of a dev agency and applied for the SaaStock Best SaaS Startup of 2018 competition as her master plan for launch. What followed were a chain of smart decisions and hard work, which led her to ultimately winning the title. Listen on to hear: How one single event determined their go to market strategy How Cristina managed to get the Cledara Virtual Debit Mastercard much faster What’s the most important feature of a Best SaaS Startup In 2019, we will be running our signature startup program at each of our events around the world. Zendesk is our global startup partner helping us support the next generation of SaaS startups. From Sao Paulo and Hong Kong, through to New York and Dublin, all the way to San Francisco to Sydney, the opportunity to fast track your growth through workshops, networking and connection will be just a short flight away at most. If you are interested in participating, send an email to gabriel@saastock.com to learn more.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

On this week’s podcast, we talk with Liam Martin, Co-founder of Time Doctor and staff.com and organiser of Running Remote, a conference devoted to leaders and executives from companies with remote work culture. We chat about hiring well and creating a healthy and strong culture remotely. Time Doctor measures remote employee productivity and staff.com acts as a two-sided marketplace for hiring remote workers. Liam eats his own dog food and both organisations are entirely remote with 100 employees spread between 26 countries worldwide. Liam started Time Doctor back in 2012 when very few companies were making the move to go for a fully remote organisation. But Liam had a perfectly good reason - the weather in Canada in winter time, which he really wanted to escape from. To make remote work, Liam has had to put in a lot of processes in place and has had to accept the reality that VC investors would not agree to fund him with such a spread organisation. Liam and his business partner have bootstrapped the company, which is currently at $5 million in ARR. Listen on to hear: What is the key ingredient to making a remote organisation effective How to create the right processes One unexpected and eye-opening tactic for hiring a healthier organisation Wherever in the world you are based, SaaStock will be landing on your continent in 2019. Unless you are in Antarctica. Just like Liam, we are not fans of thumbs-falling-off kind of freezing weather. Pick your destination. From Sao Paulo to Hong Kong and San Francisco to Sydney, we will be within a short flight at most from you so join us to learn from experienced SaaS practitioners such as Liam who are open to sharing their pitfalls, connect with peers and potential partners. And have fun, which as Liam argues is the most important thing to stay sane on this journey.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

In December of last year, we attended the first ever SaaS E[quality] unconference, organised by the Women’s Work Institute and held in Toronto, Canada. In a room of about 100 D&I champions and leaders, we had a day of fascinating stories, provocative ideas and discussions around Diversity and inclusion challenges in SaaS. On the day after the conference, I sat down for a chat with the founders of the Women’s Work Institute, Kristen Liesch and Anna Dewar Gully to hear their thoughts from all the interactions and to lay down some steps for pushing diversity and inclusion forward. A conversation we are bringing to this week's SaaS Revolution Show. Without prior experience in SaaS, Anna and Kristen approached the industry for two very specific reasons. One is that they believe the intersection of services and tech is where the best results can be achieved in terms of fixing diversity issues but also because as they reached out to leaders in different spaces to see if they would be interested in participating in a conference aiming to address this, SaaS was where they saw incredible uptake. Both Anna and Kristen are equality champions but as business strategists, they inherently believe that the topic of Diversity and Inclusion is a business objective above all and it needs to be approached as such. In that, every company should start with Why.   Listen on to learn: What problems SaaS leaders experience when it comes to D&I Why diversity and inclusion remains an unsolved issue How should each business get to a clear Why diversity matters to our business? which will be more effective in bringing improved results Improving the diversity and Inclusion at both SaaStock and SaaS is something we will be putting much more effort in 2019. By our side, we have Zendesk, our Global Diversity and Inclusion partner. We already have started the #TakingStockPledge, and look forward to doing many more initiatives throughout the year so stay tuned.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

The guest on this month's episode of The Struggle is Rory Codrington, founder of WeDelight, a customer rewards platform. His entrepreneurial journey began in 2014 when straight out of college he started the holding company that would become WeDelight. At the time his product was an action sports meetup app. After a couple of years, Rory and his CTO figured the idea wasn’t going to take off so they pivoted to WeDelight. They first operated a pay-as-you-go model and eventually switched to a subscription model. Rory still keeps a screenshot of the first Stripe payment that came through from his first customer, CharlieHR. WeDelight’s go-to-market model was simple. A focus on outbound, mainly done through email and Linkedin and this way he managed to sign some pretty notable clients. Things were trickling along but as he realised not fast enough. It was something very difficult and frustrating to deal with as he was too close to the ground and had been at it for too long to just give up. Eventually, he got a piece of very valuable advice from Ben Gateley, COO and co-founder of CharlieHR how to know it was time to fold, an experience which wasn’t easy but Rory handled with grace. Rory’s story is both inspiring and humble, filled with powerful lessons and we hope you will enjoy listening to it. If you have a story of struggle you would like to share with us, get in touch by emailing podcast@saastock.com.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

This is a reply of our most popular episode of 2018, hosting April Dunford. Seven startups. All seven of them acquired. 16 launched products. All 16 of them repositioned. Roles as varied as CEO, CMO and COO. There has never been a dull moment in April Dunford’s career. Throughout all that, she has become the world’s foremost expert on positioning. Improving the context a product creates for its customers became April’s lifelong passion. It’s why she has taken on seemingly very different roles in the various startups and their acquirers she joined. As she puts it, positioning encompasses the entire organisation. Currently, April is working on a book, which she hopes will offer the first scalable methodology for doing positioning right. Listen on to hear: Why so many startups and companies fail at positioning What are the signs you are having a positioning problem How to start fixing your positioning and create the right context for your customers Examples of product repositions April has executed What is the best way to track the effect of repositioning You can watch April's talk from SaaStock18 where she gets into much more details on all of these subjects by getting one of our SaaStock on Demand pack.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

On this short bonus episode, we take you back to our podcast stage at SaaStock18 for a chat with Olivier Pomel, CEO of Datadog. Alex and Olivier talk about how he has been hiring for hypergrowth. Originally French, Olivier moved to the US in 1999. Eight years ago he co-founded Datadog and the journey has been exhilarating and scary in equal measure. Datadog has been doubling its workforce every year and currently employs 800 people. Hiring has been one of Olivier’s main responsibilities and as he says his ability to hire has been the best predictor of future success. Datadog has a 9 figure ARR and has raised 140 million in funding. You will hear more about the founding story of the company, how Olivier has managed to double the workforce each year, how setting a clear focus early on has allowed for this and much more.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)

This week’s guest on the SaaS Revolution Show, hailing all the way from Brazil, is Diego Gomes, CEO of content marketing platform and SaaS-enabled marketplace Rock Content. Alex and Diego talk about the content marketing strategy the company has executed for their blog to reach 2 million unique visits and 50K new subscribers each month and help the company on the way to $12mm ARR. An entrepreneur by heart, Diego started Rock Content with two other co-founders, nearly six years ago. At the time they had no idea they were building a SaaS company, what made a subscription-based company successful or who else was building SaaS in Brazil. What they knew was to blog about marketing. Marketers became their core audience. Currently, at $12M in ARR, the company employs 300 people and has been profitable for three years in a row. Listen on to learn: How the customer acquisition strategy is reflected in the content marketing of Rock content What are the pillars of a truly successful content marketing strategy Whether you should be worried about the over saturation of content Diego is one of many speakers we will host at SaaStock LatAm on April 23-25th 2019 in Sao Paulo. He will be joined by Renata Centurión, from Winning by Design who will help you make sales a team sport within the organisation, Lauren Vaccarello, VP Marketing, Box who will share how to do marketing at scale, André Baldini, CEO, Superlógica Tecnologias who will walk you through how to grow 10x in three years and reach profitability and many others. Grab a ticket at a Super Early Bird rate until Friday, December 21st.    Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇮🇪 SaaStock Europe | Dublin, IrelandBook tickets: https://saastock-europe.com/🇺🇸 SaaStock USA | Austin, TexasBook tickets: https://saastock-usa.com/🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)