Mar 25, 2016 · 28m · 20vc
Immediately's Branko Cerny on The Rise Of Bottoms Up Sales and The Importance of Branding For Enterprise SaaS Companies
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Branko Cerny, founder and CEO of Immediately, to discuss how consumer design standards, mobile-first technology, and bottom-up adoption are transforming enterprise software. Cerny shares key insights on cognitive flow, building authentic B2B startup brands, and navigating early-stage venture fundraising.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 26.5% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 4.1 Guest disagreement 1.1 Harry pushing back 2.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:13 Polite rejection of congested cap table concern
Branko politely rejects Harry's framing that having 79 investors is a burden or problem, clarifying that AngelList aggregates them into a single line item.
Hardest push from Harry ▶ 20:52 Challenging guest on AngelList cap table congestionHarry cites AngelList data showing 79 investors and directly asks Branko if such a congested cap table is a problem or something weighing on his mind.
Biggest teaching moment ▶ 11:47 Explaining top-down vs bottom-up software brandingBranko educates Harry on why traditional enterprise SaaS ignored branding because sales relied on top-down VP decision-makers rather than end-user adoption.
Harry holds his own ▶ 17:04 Listing high-profile cap table investorsHarry showcases deep preparation by rattling off specific prominent angels and former podcast guests who invested in Immediately's cap table.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Immediately's Origin Story and Cognitive Science | 1 | 4 | 1 | 0 | Harry opens with an open-ended question about Immediately's origin story. Branko delivers an extended monologue detailing his background studying cognitive science and explaining how technology disruption impacts focus and flow state. | |
| Navigating Enterprise SaaS as a Young CEO | 2 | 4 | 1 | 2 | Harry asks about the challenges of being a young CEO in an enterprise SaaS sector dominated by older executives. Branko acknowledges the experience gap but reframes his youth as an unfair advantage due to his empathy with millennial salespeople. | |
| Consumerization of Enterprise Software | 3 | 5 | 1 | 1 | Harry connects the discussion to Slack and asks if this represents a broader shift toward bottom-up enterprise adoption. Branko explains consumerization trends, citing how changing millennial expectations impact enterprise software adoption. | |
| Mobile-First Strategy and Sales Lifestyle | 3 | 5 | 1 | 3 | Harry presses on why enterprise software has historically lacked branding and how a company can practically cultivate a consumer-style brand image. Branko breaks down traditional top-down sales vs modern user-centric brand empathy. | |
| Cap Table Strategy and Building Investor Trust | 4 | 4 | 1 | 2 | Harry demonstrates familiarity with Immediately's cap table by naming several prominent investors and previous podcast guests. Branko elaborates on seed-stage fundraising dynamics, emphasizing trust and seed extension expectations. | |
| Balancing Thoughtfulness and Execution Speed | 4 | 4 | 2 | 4 | Harry challenges Branko by bringing up AngelList data showing 79 investors and asking if a congested cap table is a burden. Branko gently corrects the premise by explaining that AngelList operates as a single SPV line item. | |
| Quick Fire Round | 3 | 3 | 1 | 3 | Harry conducts a quick-fire round, pushing Branko to reflect on early fundraising mistakes. Branko candidly admits to going out too early and learning from taking 30 initial rejections. |
Statements from this episode (12)
Cerny: Cognitive science shows 15 minutes needed for task immersion
“Cognitive science tells us that it takes up to 15 minutes to really fully immerse yourself in a task”
Cerny: Unaligned sales tools force reps to contort their process
“When the technology doesn't map onto how a salesperson would optimally want to run that conversation, it actually becomes a hindrance. The rep has to contort themselves and their sales process to the inadequate tool that they have at their disposal.”
Cerny: Younger workers will seek workarounds rather than use legacy CRMs
“More and more of today's entry-level workforce generation will often just not put up with clunky software. When you think about how they live, First thing they do after they open their eyes in the morning is check their Instagram, check their Tinder, and hit t…”
Cerny: Successful sales software must deliver a lifestyle, not just utility
“A key insight that we had early on was that in order to be successful with salespeople, we can't just build and sell a piece of software. What we're bringing to the market is a lifestyle. It's an aspirational lifestyle that is more in keeping with what motivat…”
Cerny: Modern sales reps are no longer solely motivated by money
“There's this old perception of the coin operated salesperson is just motivated by money, but that couldn't be further from the further away from today's reality.”
Cerny: Immediately employees must speak with a user every workday
“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 to talk to at least one user or one customer every single day.”
Cerny: Hiring consumer agencies produces inauthentic enterprise SaaS brands
“You can try to hire like a LA brand firm that, that worked with Snapchat and Tinder and have them try and kind of craft the brand for you. But I think it will just come off as inauthentic if you're not actually living it inside of the company.”
Cerny: Cap table selection should prioritize trust and founder vulnerability
“Silicon Valley is a really small place, and to me, the rule of thumb of who I want on my cap table and how I think about meeting investors and bringing them on board is, do I, in my gut, feel like I can trust this person? Like, I can be vulnerable with them an…”
Cerny: Smart seed investors back high founder learning velocity
“And I think the smartest seed investors are investing in, in the founder's ability to use the seed capital to really figure out the answers to some really hard questions that have never previously been answered and make a lot of mistakes along the way, but lea…”
Cerny: Immediately mandates work-from-home Monday mornings for weekly planning
“The number one value that we have at immediately is thoughtfulness. For instance everybody gets to work from home Monday morning until noon, because then at noon, everybody's expected to come in and have really thought through how they want to invest the most …”
Cerny: Founders shouldn't raise until convinced investors would be remiss passing
“Don't go out until you're ready. I think a lot of founders kind of take whatever, whatever piece of wisdom or truism they get about, you should be raising when you have six months runway left, or when you get your first or third customer, whatever it is, that'…”