Grow & Tell

Robby Allen, CRO of AgentSync, shares sales leadership stories from his time as Director of Sales Development at Zenefits.Zenefits is one of the most infamous hypergrowth stories in SaaS history, growing to over $70 million ARR and a $4 billion valuation from 2013 to 2016.But their hypergrowth came at a cost. Insurance compliance issues resulted in millions of dollars of fines, a leadership shakeup, and mass layoffs in 2017.Robby Allen was there for all of it — bringing some key lessons from Zenefits to his next venture, leading sales at AgentSync.On today's episode, Alex and Robby discuss:Transitioning from SDR to sales leaderSpinning up Zenefits' outbound strategyWhy AgentSync hired scrappy AEs before enterprise repsThe difference between being a CRO and VP of SalesWorking with Jason Lemkin at SaaStr

Chris Orlob shares his unlikely origin story as Gong's first marketer, sales leadership advice, and what it was like to transition entrepreneurship at Pclub.In 2015, Chris faced tough competition when his newly founded company, Conversature, went up against Gong -- the eventual category winner.Although he was forced to close his doors just one year later, a new one opened at Gong.After joining as Gong's Head of Product Marketing, Chris started Gong Labs, one of the most successful content marketing programs in SaaS, and helped grow Gong from $200k to $200M ARR and a $7.2B valuation.In 2022, he left Gong and leveraged his audience into co-founding Pclub.io — a sales learning platform, and QuotaSignal — a tech-enabled revenue team hiring service.On today's episode, Alex and Chris discuss:Going from competitor to Product Marketing Director at GongThe explosive growth of Gong LabsTransitioning from marketing to sales leadershipCo-Founding Pclub.io and QuotaSignal

Todd Busler shares how his path from first go-to-market hire to VP of Sales at Heap led him to found his own tech company, Champify.Being an early sales hire is a great test run for being a founder.As the first sales hire at Heap, Todd helped the company grow from $300k to $40 million ARR and 10x their average contract value.Six years later, he co-founded Champify, helping GTM teams sell more effectively with one innovative tool.In today’s episode, Alex and Todd discuss:How internal sales competition led to Heap’s growthThe evolution of Heap's competitive messagingHow the sales landscape has changed over timeThe differences between being an early sales hire vs. a founder

Nico Dato, CMO of Entrata, shares lessons from growing Podium from a single-product review platform to a nine-figure, multi-product lead gen platform.When Nico Dato joined Podium in 2015, they were a single-product review tool for SMBs with under $1m in revenue.Over a 7-year period, Nico helped grow Podium to a multi-product lead conversion platform with over $100m in revenue. For those counting at home, that's 100x growth.In today’s episode, Alex and Nico discuss:How Podium grew primarily through webinars and industry tradeshowsThe two most important relationships for every marketing leader (spoiler: it's Product and Sales)Why MQLs are a deceptive metricPlanning Entrata's massive user conferenceWhy you shouldn’t sleep on Utah as a tech hub

Marie Gassée, Head of Go-to-market at Column, shares stories of growing self-serve at Box and Confluent.Marie Gassée has an impressive track record building growth programs.She led the launch of Box’s product-led motion and helped Confluent commercialize its open-source developer community.But none of that growth came easy.On today's episode, join Alex & Marie as they discuss:Building Box’s self-serve programSelling to open-source users at ConfluentEarly growth lessons from ColumnScaling herself along her career journey

Joseph Schmitt, VP of Success at UpKeep, shares his learn-by-doing approach to growing Customer Success teams. Joseph Schmitt is exactly the type of growth story we like to tell—from a few perspectives.He’s had a surprisingly fast personal career arc from entry-level support to senior Customer Success leader and also helped grow two startup customer success teams from the ground up.On today’s show, Joseph and Alex chat about:Transitioning from entry-level support to management & senior leadershipJoining UpKeep as their first CS hireHiring and retaining UpKeep’s CS team for the past 6 yearsStructuring UpKeep’s CS teamsWorking with a non-tech-savvy customer baseAdvice for early CS hires

Peep Laja, co-founder of Wynter, CXL, and Speero, shares lessons from bootstrapping multi-million-dollar businesses from scratch. Plus, he shares messaging lessons from Wynter.Peep Laja is an expert at bootstrapping companies.He started by turning his in-house marketing experience into a consultancy…He took that consultancy and scaled it into an agency…He used the profits from his agency to bootstrap an e-learning business…And then he took the profits from his elearning business to bootstrap a SaaS company.In today’s episode, Peep and I discuss:The founding stories behind his three companiesAdvice for company positioning and messagingWhy he moves upmarket as fast as possibleWynter’s growth and marketing strategy

Peter Kazanjy, co-founder of Atrium and author of Founding Sales, shares sales advice for startup founders. They discuss pivoting startups, democratizing sales metrics, datafication of sales, and building a sales community. The conversation also covers the evolution of sales processes, community marketing, navigating product development for revenue teams, and the consolidation of sales tech.

Former Head of Marketing at Notion, Camille Ricketts, shares insights on positioning Notion as a broad product, building an engaged community, partnering with influencers, infusing emotion into marketing strategy, and advice for community-led growth.

Gillian Heltai, Chief Customer Officer at Lattice, shares her experience in building customer experience programs at Lattice, Talkdesk, and comScore.As Gillian puts it, she worked in customer success long before anyone called it customer success.Since then, she's helped build successful CX programs at comScore, Talkdesk, and now Lattice.On today's episode, Alex and Gillian discuss:Growing from entry-level analyst to Senior VP at comScoreGoing on a customer listening tour at Talkdesk to create a new onboarding program for upmarket customersJoining Lattice after its Series CHow Lattice structures its CX teamsAdvice for onboarding, health scoring, renewals, and more