The Scale Up Show

Ryan interviews Stefan Smulders, founder and chief strategy officer of Expandi, a LinkedIn automation SaaS company. Stefan shares how he bootstrapped Expandi to $8 million in ARR in just 4 years through relentless hustling, including doing over 700 product demos in the first 3 months. He emphasizes the power of inbound marketing through valuable content creation, building a personal brand with his face on it, and capturing leads into a tight community. Stefan also stresses the importance of focusing on reducing churn by improving onboarding and guidance instead of only chasing new signups. With the right team in place to solve these challenges, he’s confident Expandi can scale to $20 million ARR quickly. Tune in to hear Stefan’s energy, insights and unique story on growth marketing and scaling on LinkedIn.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS:

• Stefan completed over 700 product demos in first 3 months to validate product-market fit and learn users' needs
• Expandi focused on inbound marketing through content creation and giveaways to build an audience
• Stefan his personal story and face on the brand to stand out and build trust
• Expandi captured leads into the community, to build relationships and get feedback
• 90% of new signups still come from content and inbound marketing
• The biggest challenge now for Expandi is reducing churn by improving onboarding
• With the right team, Stefan is confident Exapndi can rapidly scale from $8M to $20M ARR
• Relentless hustling and grind in the early days was key to explosive growth

BEST MOMENTS

"I was working around 16, 17 hours a day and mainly running demos."

"We started heavily to distribute all these pieces of content and that drove so many people."

"If you really understand what's the pain points of the people you want to reach, you can easily host live sessions.”

"The biggest transition I needed to understand and make was, okay, we need to leverage data-driven approaches."

"If we can solve both of them [problems] and we are working on a daily base, we will grow to 20 million within no time."

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Ryan is joined in this episode by Ori Keren, founder and CEO of LinearB, a software delivery management company nearing unicorn status. Ori shares how he and his co-founder built the company remotely, him in Tel Aviv and his partner in California. He outlines LinearB's growth strategy of focusing on the mid-market before expanding to enterprise. Ori stresses the importance of constantly evolving based on customer feedback. He also discusses key challenges around scaling the company efficiently and how LinearB is leveraging AI, using it to build internal tools that increase productivity.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS:

• Ori and his co-founder built strong trust by working together previously, enabling them to scale a remote company.
• LinearB found product-market fit by staying focused on the mid-market before expanding upmarket.
• They grew rapidly by releasing MVPs, gathering customer feedback, and quickly iterating.
• Efficient growth and scaling teams 10x in size are their current scaling challenges.
• LinearB is using AI to build internal tools that drive productivity.
• Engineering leaders are an underserved audience that crave content, now more than ever.

BEST MOMENTS

"Being a co-founder with someone is sometimes more intense than a marriage."

"We weren't tempted to go after enterprise customers. We stayed focused on mid-market's high-velocity end-to-end sales cycle."

"If you really want engineering teams to improve, you've got to democratize the data."

"It's not enough to just spot problems, you need to program workflows to solve them."

"Engineering leaders are lonely. It's a very lonely job."

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Ryan interviews Greg Rich, CEO of Vivantio, a SaaS company providing service management solutions. Greg started working in customer service at age 13 in his family's business and co-founded Vivantio in the early 2000s to fill a gap in the market for cloud-based service management software.

Greg talks about keeping up with rapid advancements in AI and using it to improve customer experiences. He shares how Vivantio scaled from nothing to $5 million in ARR through channel partnerships, expanding to the large U.S. market, and focusing on customer education. Greg discusses the challenges of scaling marketing and sales as Vivantio transitions to a high-growth organization. Tune in to hear Greg’s unique origin story and his vision to reach $20 million ARR in the next few years.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• Greg Identified an untapped market for cloud-based service management SaaS in the early 2000s.
• He leveraged partnerships to fill the sales gap without significant cost early on. Greg was also creative in using low-cost marketing and pay-per-click to grow.
• Vivantio focuses messaging on educating customers about service optimization, education is key and Greg’s customer service background has enabled him to create and foster a customer-centric culture.
• Vivantio expanded to the U.S. in 2011, and now 50% of revenue comes from the U.S. market.
• Greg has developed tech to leverage customer data and AI to provide industry benchmarking as well as predictive analysis.
• The biggest challenge when transitioning to high growth is scaling marketing and sales.

BEST MOMENTS

“One of the first things we did was realize that Russ and I weren't sales and marketing people...how do we fill that gap without the money to pay people?"

"We leveraged our relationship with partners who were able to fill that gap we didn't have."

"Now 50 per cent of our customers are in the U.S."

"My biggest challenge is go-to-market - how do we scale, reach more people, get our message across succinctly?"

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES
www.vivantio.com

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Two-time founder and current VC investor Harpinder (Harpi) Singh joins Ryan in this episode. His firm, Innovation Endeavors was co-founded by the CEO of Google Eric Schmidt and they have invested in many companies including Uber. Harpi gives the interesting insights he has gained at a macro level of the start-up scene and talks about what you can do to make yourself more attractive for funding in the current climate. If you are looking at funding or just want to know what’s happening in the start-up space, particularly around the utilisation of AI this is an episode not to miss!

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• Harpi met his founding team at Standford, sold 6 ½ years later, building another start-up which he then also sold.
• Having two to three founders appears to be the sweet spot for success for start-ups.
• As a start-up, you’re in a race against time to find product market fit and go-to-market and you want to try and do this as quickly as possible with the lowest cost. If you can focus on the right KPIs this can aid you with both things.
• The toolkit that is available now to start-ups just got 10x bigger and better. They are now able to utilise AI and associated technologies faster and more effectively due to their agility and ability to take on more risks.
• Chat GPT releasing an enterprise-specific AI will have a large impact on the marketplace, especially alongside Microsoft and Google releasing their own too.
• If you’re an enterprise, you really need AI software that is end-to-end so you aren’t having to add the complexity of merging tools.
• Harpi’s top 3 tips for a company to be highly investable is to create a must-have product. Be vigilant about the feedback you get back from the market and only act based on it.
• Founding in an economic downturn doesn’t have to be difficult it has its own unique opportunities such as being able to hire easily.

BEST MOMENTS

“With new data and compute you are able to come up with automation, with decisions making that’s much faster”

“The fundamental advantage start-up companies have is the speed up iteration”

“Almost every founder I talk to says they wish they had a co-founder”

“People are using AI to give super powers to their people”

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES
https://www.innovationendeavors.com

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

 Dmitri Adler is the cofounder of Data Society which is an award-winning AI software and engineering firm serving the enterprise and service sectors. Data Society is one of Ink 5000 fastest growing companies and also one of the top ten ed-tech companies identified by Forbes! They bootstrapped themselves to $10 million using process-driven customer service and AI. Dmitri joins Ryan to discuss how they have achieved all of this and specifically highlights how to collect relevant data and the importance of AI literacy.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• The skills and expertise execution of Data Society’s team paired with excellent customer service is why they have such good customer retention.
• Finding various yet consistent ways to drive value for their clients is one of Data Society’s core values.
• Processes to quantify customer feedback have been essential, Data Society ensures they do customer evaluation at multiple steps throughout the customers' journey.
• Humans are social animals and learning solo can be limiting. If you learn with others, such as your colleagues, it can be a lot more effective.
• Data Society tailors their programmes to clients’ use cases, ensuring it’s actionable means that it has a higher retention rate; people stick with it.
• We use AI to either do something by following a pattern or to make a recommendation based on a pattern it has learnt from. So, your organisation needs to be able to collect relevant data to utilise AI effectively.
• AI is a great impersonator and learning from people but when people can’t discern what is real and what isn’t from AI, that creates a distortion of the world and will lead to bad decisions.

BEST MOMENTS

“We’re focused on the enterprise, it’s very much about customer service”

“Customers come back when you do a good job”

“We’ve stuck to our guns in terms of what we’re very good at”

“If you want to use AI you have to have data that it can learn from and that it can utilise in order to tell you something”

“The most dangerous thing about AI is when you don’t know what it is doing, it’s powerful”

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Vinay Patankar is a three-time founder, including Process Street, an AI-powered process management platform that started with a workflow product. Vinay shares his experience of being a digital nomad for 10 years and how it inspired him to create Process Street. Ryan and Vinay also talk about the democratization of AI and the biggest value they think it will add to businesses.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• Vinay began working as a digital nomad, doing this meant he had to create his own work as remote working wasn’t really a thing yet. He began creating a series of internet companies including SEO sites and selling other services.
• When he had 20 people on his team, Vinay started to feel overwhelmed by the management aspects, it became a personal pain and that’s what led to the creation of Process Street.
• A lot of AI products that are and will continue to be launched are to make repetitive processes more efficient or higher quality.
• Humans don’t like doing repetitive work but it is required for human prosperity, this is how AI can aid us.
• Human quality control and unique creativity are not things AI can replicate but most other things can be automated.
• HR, finance and real estate are the three main industries Vinay aids with his products.
• Process Street is similar to a lot of collaboration platforms but its main difference is Process Street has a builder and collaborator user model.

BEST MOMENTS

“Why isn’t there a software that does this for me, it felt like what I was doing was very repetitive”.

“The biggest value AI is going to add is the execution of these repetitive processes”

“I see it as just another form of automation”

“You can manipulate data in interesting ways”

“We don’t want to be creative in these scenarios, there are parts of businesses and types of businesses where you don't want that creativity"

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Lloyed Lobo is the founder of Boast AI. He scaled from zero to $10mil+ and all with no investment! Lloyed created an entire community, utilizing this community for growth and now has written a book about it. He talks to Ryan about how you can grow and lead a movement from scratch and then leverage it for your next opportunity and gives an amazing breakdown of how to bootstrap your way through building a business, avoiding giving up your freedom and equity to investors.

Grab LLoyed's entire GTM community led growth playbook here in his Top Selling Book: From Grassroots To Greatness: 13 Rules to Build Iconic Brands with Community Led Growth: Grab the Book 

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• Entrepreneurship is all about taking something from nothing and dealing with risk and uncertainty to create a positive outcome
• After the advice from an entrepreneur, Lloyed took a sales job to learn the skills needed to be a successful entrepreneur.
• One of the best ways to bootstrap a company to $ 1 million plus ARR is to sell a service.
• Lloyed first started the company from his bedroom, he had to get very good at communicating with his customers and learning exactly what they wanted. They didn’t have anything else they could rely on.
• When starting out, talk to your customers to find out what their pain points are and discover what they need. You need to do things that are manual and won’t scale in the beginning.
• Think about the bigger picture and the wider purpose of your product, connect with your customers and help enable their success.
• Utilise other people’s credibility and brand reputation by collaborating with them.
• Get back to basics with your marketing and branding, simple can be very effective especially if you utilise tried and tested methods.

BEST MOMENTS

“You attract the energy you give out”

“I used to procrastinate on everything”

“Everything you do as an entrepreneur is all communication”

“You won’t know exactly what to build if you don’t do the work manually…do things that don’t scale in the beginning”

“You’re asking about the problem, not the solution”

“Building a service is a great way to bootstrap it”

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES
https://www.linkedin.com/in/lloyedlobo/

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Gaurav Oberoi is the CEO and co-founder of Lexion.ai, a generative AI in the legal space. He is a 4x founder and was also a former VP of Product and survey monkey. Gaurav joins Ryan to talk about how to tactically create a mode with AI, how to get the best product market fit and the importance of time to value and demonstrating high-value ROI early on.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• Lexion.ai makes software that helps companies accelerate the entire contracting process. They bring AI and acceleration to every part of the process.
• Linkedin is a great social platform to leverage, you can put content out there that provides value and also notifies people of your business at the same time
• It’s essential to focus on delivering a very high-quality product with high ROI otherwise having a good referral engine is useless.
• Positive feedback isn’t all you need to build a product, you need commitment from your early interest clients as well as the ability to read between the lines and push for the harder feedback that isn’t always immediately obvious.
• AI is quickly becoming more sophisticated but it still has a lot of limitations such as when something has been done incorrectly or where more context is needed.
• When using AI you need to teach it your personal rules, all the context it may need, generate guard rails and remember that it will constantly be evolving and you are driving that evolution.
• If you want to grow a start-up then you need to show high value quickly, the faster and more clearly you can show the ROI the better.

BEST MOMENTS

“Our software is all about any kind of document process that needs accelerating”

“Nowadays the most powerful social network for b2b companies is LinkedIn”

“It’s not really when people have paid that you’ve got success, it’s really when you see repeat usage that you know it’s working”

“Having significant data about users and their activity is a significant mode”

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

This show was brought to you by Progressive Media

Matthew Tillman is the CEO of OpenEnvoy and has worked in the machine-learning space for over 20 years. Matthew talks to Ryan about how he built his solution to generate 38x ROI for his customers, where to spend your time in your start-up as well as machine learning and the role of AI in reimagining what is possible.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS

• OpenEnvoy replaces complex accounts payable processes by replacing human-centric workflows with AI.
• One of the ways to overcome many go-to-market challenges is to hire a team that has the right skills to both create value and demonstrate it effectively to your customers.
• Matthew recognised there was a problem in the accounts payable industry as none of the companies could handle variable cost invoices, so he set out to fix it.
• As a founder, you have to recognise what things are worth delving into deeply and what ideas and thoughts need to be put ‘on the back burner’. It can be too easy to investigate and get involved in anything to do with your business as you have so much passion for it.
• Focus on your business and what you can do more of today to grow it.
• Customer feedback is always an opportunity, the information you get is invaluable.
• Think about which people can add value to your business but also who you as a leader and founder can add value to, to get the most out of your people.
• Focus on the customers who will love you and therefore will refer you, this is one of the least optimized customer acquisition levers.
• Machine learning and tech are so much cheaper, in many cases even free. This wasn’t possible 20 years ago; it has democratised many industries.
• Opensource tech means you get an incredible amount of feedback whilst having to provide a lot less value.
• Matthew believes that AI gives us the opportunity to stop treating humans like robots, finding solutions to help find them value-add work to do instead of treating people poorly.
• Demonstrating a 38x ROI for his customers proves that the OpenEnvoy solution is providing incredible value.

BEST MOMENTS

“All founders have to be insanely passionate about whatever they’re working on”

“I love hearing from customers, good or bad”

“It’s really important to nail your schedule”

“You optimize towards customers that will love you and refer you”

“The reality is machines do this black and white input better than you can handle it”

Ryan Staley

Founder and CEO

Whale Boss

[email protected]

www.ryanstaley.io 

EPISODE RESOURCES

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets