Immediately's Branko Cerny on The Rise Of Bottoms Up Sales and The Importance of Branding For Enterprise SaaS Companies

In this episode of "20 Minutes VC," host Harry Stebbings interviews Branco Cherny, the founder and CEO of Immediately, a mobile platform designed to enhance sales through relationship-driven strategies. Cherny discusses the importance of technology that supports, rather than hinders, productivity and the concept of flow. He emphasizes the shift in enterprise SaaS towards a user-first approach, citing the rise of the millennial workforce's influence on technology adoption. Cherny also touches on the challenges and advantages of being a young CEO in the enterprise space and the significance of building a brand that resonates with users' lifestyles. The conversation covers the investment landscape, with Cherny sharing insights from his fundraising experiences and the value of trust between founders and investors. He highlights the role of empathy in marketing and brand-building, and how companies like Slack and Greenhouse are leading the way in user-centric enterprise solutions.

• "20 Minutes VC" is a podcast hosted by Harry Stebings.
• Branco Cherny, founder and CEO of Immediately, is the guest for "Founders Friday."
• Immediately is a mobile platform designed for modern sales professionals.
• The platform aims to revitalize sales as a relationship-driven craft.
• Investors include Naval Ravikant, Ryan Holmes, Jonathan Abrams, and Kate Shillo.
• Kate Shillo facilitated the introduction for this interview.
• Sanebox is endorsed as a tool for email management, offering a special deal to podcast listeners.

This is the 20 minutes VC with your host, Harry Stebings. And before we welcome in the weekend, I'm delighted to bring you another fantastic founder joining us for founders Friday today, Branco Cherny is the founder and CEO at immediately...

This quote introduces the podcast episode and its guest, Branco Cherny, setting the stage for the conversation about entrepreneurship and technology.

• Branco Cherny is passionate about understanding human behavior and cognition.
• His interest lies in what drives people to experience "flow" and how technology impacts productivity.
• Observations of the ubiquity of iPhones and its distractions during his college years sparked his interest in productivity technology.
• Cherny and his co-founder began by addressing mobile email inefficiencies.
• They pivoted to focus on sales, seeing it as a series of conversations hindered by inadequate technology.
• The goal of Immediately is to create a user environment that enables perfect flow for salespeople, making business transactions smoother.

Yeah, well, my biggest passion in life is better understanding how we humans work... I kind of realized, wow, it becomes borderline impossible to maintain full focus on a task for more than five minutes...

This quote explains Cherny's initial interest in human cognition and how it led him to explore the intersection of technology and productivity, eventually inspiring the creation of Immediately.

• Branco Cherny often finds himself as the youngest in gatherings of enterprise SaaS CEOs.
• He focuses on listening and learning from experienced peers to gain pattern recognition and best practices.
• Cherny views his youth as an advantage because it allows him to approach problems with a fresh perspective.
• Immediately adopts a bottom-up distribution model, focusing on the end-user first.
• The company's target audience is the millennial salesperson, which aligns with Cherny's demographic, allowing for greater empathy and innovation.

Yeah, that's a good question. It's totally know... We are an enterprise SaaS company, but we are strongly a bottom up distribution model, which means that we focus on the user. 1st, second and third is the only thing we obsess about.

This quote addresses the unique position Cherny holds as a young CEO in the enterprise space, highlighting both the challenges he faces and the distinct advantages he brings to his company.## User-First Approach in Enterprise Technology

• The current trend in enterprise technology focuses on user experience.
• Companies are adopting a "roots up" approach rather than targeting specific enterprise decision-makers.
• This shift is partly due to the changing expectations of technology among millennials.

"Is this the symbolism of a new wave of enterprise technology, do you think, in the past couple of years, where users have become first, and we're not selling to particular people in the enterprise, and we're not trying to impress them, we're going for the roots up approach?"

The quote questions if the user-first approach symbolizes a new trend in enterprise technology, suggesting a significant shift from traditional top-down sales models to prioritizing end-user experience.

• Consumer technology trends influence enterprise software expectations.
• Millennials expect seamless, efficient technology that integrates naturally into their lives.
• Sales software and other enterprise tools are experiencing friction due to outdated user experiences.
• The younger workforce often seeks alternatives to cumbersome enterprise technologies.

"Consumerization of the enterprise is a very real trend."

This quote confirms the ongoing trend where consumer technology preferences are shaping expectations in the enterprise environment.

• Millennials prioritize technology that aligns with their lifestyle and habits.
• Enterprise technology must reflect the ease of use found in personal apps like Instagram and Tinder.
• The new generation resists using outdated enterprise solutions, preferring brands that speak directly to them.

"More and more of today's entry level workforce generation will often just not put up with clunky software."

The quote highlights the intolerance of the younger workforce towards inefficient enterprise software, stressing the need for a user-centric approach in design and functionality.

• Immediately adopted a mobile-first approach to cater to the on-demand workforce.
• The strategy aims to support a lifestyle where work is integrated seamlessly with personal life.
• Sales representatives prefer tools that allow them to work dynamically and build relationships outside of a traditional office setting.

"We have to build from mobile first, because we need to build a product that is powerful and elegant, but mainly that the sales rep can bring with them anywhere that the customer is and anywhere that their lifestyle takes them."

This quote explains the rationale behind a mobile-first product strategy, emphasizing the need for flexibility and mobility in modern sales environments.

• Building a brand that resonates with the end-user is crucial for modern enterprise software companies.
• Traditional enterprise software companies focused on decision-makers at the top, neglecting the end-user's preferences.
• A relatable brand is becoming essential as millennials demand tools that reflect their personal brand affiliations.

"It's extremely important to us, and I think it's the great tragedy of enterprise software."

The quote signifies the critical role of brand building in enterprise software, which has been historically overlooked, suggesting a shift towards creating a consumer lifestyle brand within the enterprise.

• The traditional top-down sales model is becoming less effective as end-users gain influence over technology adoption.
• Millennials in the workforce are vocal about their preferences and may refuse to use tools that hinder their productivity.
• Enterprise companies must consider the personal brands and lifestyles of their end-users when developing products and brands.

"You don't really give a shit if the end user wants to use your product or not, as long as you get the contract sign. But that is really changing today..."

The quote emphasizes the changing dynamics in enterprise sales, with a growing focus on the end-user's willingness to use and adopt the product, rather than just securing a contract with decision-makers.## Empathy in Marketing

• Empathy is crucial for effective marketing in enterprise companies.
• Understanding the target audience's mindset, lifestyle, and passions is essential.
• Direct contact with customers fosters a connection that informs marketing strategies.
• Authenticity in branding requires a company to embody and live the brand values.
• Employees, including software engineers, must relate to customers and their needs.

"The way that we run things that immediately, for instance, the number one priority, we say, if nothing else happens in your workday, you have to have talked to at least one user, one customer, every single day."

This quote emphasizes the importance of daily customer interaction to maintain a strong connection and empathy with the end user, which is a top priority in the company's operations.

"You have to live it in order for the brand to feel authentic."

The relevance of this quote lies in the idea that authenticity in branding comes from a genuine understanding and embodiment of the brand by everyone in the company.

• Companies like Slack and Greenhouse are cited as examples of successful branding.
• These companies focus on selling a lifestyle or experience rather than just a product.
• Effective messaging and technology are tailored to the end user's needs.

"There are certainly companies that are doing a really good job compared to kind of what we're used to."

This quote acknowledges that some enterprise companies have successfully conveyed their brand by focusing on the user experience and lifestyle enhancement.

• Trust and personal connections are key in the seed investment stage.
• Founders should seek investors who they can be honest and vulnerable with.
• The ability to learn from mistakes and adapt is valued by smart seed investors.
• Seed extensions often rely on established trust between founders and investors.

"Investment at the seed stage is an extremely personal process."

This quote underlines the personal nature of early-stage investment, where the relationship and trust between investors and founders are crucial.

"That really is just an exercise in trust."

The relevance of this quote is the emphasis on trust as the foundation for ongoing support and investment in a startup.

• The company values both rapid iteration and thoughtful planning.
• Employees are encouraged to be thoughtful about their time investment.
• Adapting business models quickly can be necessary, but must be based on thoughtful communication.

"The number one value that we have at immediately is thoughtfulness."

This quote highlights the company's prioritization of thoughtfulness in decision-making and time management.

"We have done things like completely make 180 on our business model week over week."

The relevance of this quote is the company's agility in making significant business model changes while maintaining a thoughtful approach.

• A large number of investors can be managed effectively through vehicles like AngelList.
• Each investor contributes to the company's progress.
• A congested cap table is not a significant concern if managed properly.

"It doesn't weigh on my mind all that much."

This quote indicates that the speaker is not overly concerned about having a large number of investors, as they are managed as a single line item on the cap table.

"Every single one of them has in some sense been instrumental to getting us where we are."

The relevance of this quote is the acknowledgment of the positive impact each investor has had on the company's journey.## Importance of Selective Investor Inclusion

• Inviting a broad range of supporters is beneficial for first-time founders.
• Having a large team of supporters can alleviate the burden of startup challenges.

And looking ahead, we're now at the point where we're only going to be in every subsequent round adding one or two or potentially three new line items to the cap table because it's all going to be larger institutional checks and so don't overdo anything.

This quote emphasizes the strategy of being selective with investor inclusion in future funding rounds, focusing on larger institutional checks rather than numerous small investors.

• Branco Cherny values the First Round Review for sales content.
• Participates in Pete Kazanji's modern Salesforce salon for sales insights.
• Appreciates Nerial's writing on building habit-forming products.

Yeah, I think the first round review has consistently some of the highest quality content on the sales side.

Branco Cherny recommends the First Round Review for its quality sales content, indicating its influence on his professional development and strategies.

• Founders should only seek funding when confident in their venture's value.
• Premature fundraising can result in wasted time and effort.

You should be raising when in your mind you are truly, genuinely, in your heart of hearts convinced that the investor would be remiss not to make the investment.

This quote captures the essence of strategic fundraising, suggesting that founders should only approach investors when they believe in the undeniable potential of their business.

• Moleskine notebook and pen are essential for high-quality thinking.
• Intercom is a favored tool for user communication within the company.

The real productivity tool is a moleskine notebook and a pen.

Branco Cherny finds traditional note-taking crucial for thoughtful decision-making, highlighting the value of simplicity in productivity.

• Branco Cherny enjoyed "American Gods" by Neil Gaiman.
• Finds parallels between the book's themes and Silicon Valley culture.

I found it strangely applicable to the world in Silicon Valley, where we kind of create heroes and assign heroic status to companies and founders who are just mere humans.

The quote reveals Branco Cherny's perspective on Silicon Valley's tendency to idolize founders and companies, resonating with themes from "American Gods."

• Aim to be the preferred environment for business transactions.
• Focus on creating intelligent tools that facilitate better transactions.
• Enhance the fundamental human aspect of sales and relationships.

If we can create a suite of really intelligent tools that combine into the ecosystem where a salesperson and potentially even the customer benefit from the technology, really facilitating as good a transaction as possible, eliminate the information problem and just bring sales and business transactions back to their fundamentals.

This quote outlines the goal of developing a suite of intelligent tools designed to improve sales transactions and address the information challenges in business dealings.

• Harry Stebings encourages listeners to explore the Sasta podcast for in-depth SaaS insights.
• Promotes sanebox for email management and offers a special deal for listeners.

And if you enjoyed our deep dive into the world of enterprise SaaS, then you must check out the official Sasta podcast brought to you by Jason Lempkin at Sasta and I.

Harry Stebings recommends the Sasta podcast for further exploration of the SaaS industry, suggesting it as a valuable resource for listeners interested in the sector.