Grow & Tell

Open AI's Conor Dragomanovich shares his personal sales career growth story at Productboard, where he went from founding AE to VP of Commercial Sales in only 5 years.As a two-time founding AE, Conor Dragomanovich knows all about what it takes to start and build a successful sales team.On today's episode, Conor and Alex chat aboutProductboard's early product-led sales processWhat it was like to transition into an enterprise roleThe transition from managing reps to managing managersHow to hire a founding AEWhat sales looks like at OpenAI

Chris Gadek, CRO at AdQuick, shares the company's growth story and best practices for out-of-home advertising in B2B.Out-of-home advertising is one of the most underrated strategies for B2B startups.Billboards might feel like a tactic reserved for large corporations, but Chris Gadek from AdQuick actually recommends them for Series A startups.That's why he's joining us for a crash course on running out-of-home ads.On this week's episode, Alex and Chris discuss:Building AdQuick's two-sided marketplaceHow AdQuick digitized an old-school industryWhat you need to run a strong billboard campaign

Lish Barber, Senior Director of Enablement at Sigma Computing, shares stories and lessons from building early enablement programs at iHeartMedia, Algolia, and Sigma Computing.After starting her career in sales at iHeartMedia, Lish Barber accidentally fell into a sales operations role overnight. It was there that she started her long career in enablement — building programs for technical products like Algolia and Lattice before landing her current role at Sigma Computing.In today's episode, Lish and Alex talk all things enablement, including:How to balance product vs. process in technical sales education What goes into a great sales kickoffWhere sales enablement sits on a cross-functional teamWhat tools should be in every enablement tech stack

Pete Hancock, former VP of National Sales at Yelp and current SVP of Global Sales at Restream, shares stories from the early days of Yelp's go-to-market plan.During his 11 years at Yelp, Pete Hancock helped the then-startup grow from $1m in revenue to over $750m.He also built a rigorous sales program that trained thousands of AEs.In this episode, Alex and Pete discuss:What sales looked like in the earliest days of YelpYelp’s intense sales training programHow they built a community marketplace around the productPete’s transition to selling national accountsThe impact Yelp’s sales culture has had on the broader industry

Kyle Norton, a seasoned sales leader who has driven revenue at companies like League and Shopify, shares insights from his dynamic career. He discusses the challenges of building sales teams from scratch and pivots in strategy during rapid growth phases. Norton emphasizes the importance of customer-centric approaches, especially during crises like the pandemic. He also highlights his transition from Shopify to Owner, emphasizing mentorship's role in navigating startup challenges and the value of maintaining mental health in high-pressure environments.

Hector Hernandez, CRO at Teleport, shares sales lessons from taking two developer-focused platforms — LaunchDarkly and Teleport — upmarket.When Hector Hernandez joined LaunchDarkly in 2017, they already had $1 million in revenue. Instead of focusing just on scaling, they were looking for a sales team to help them evolve past their PLG motion.Since then, Hector has helped LaunchDarkly grow to over $60M in revenue and a $3B valuation.3 years later, he repeated his success with Traceable AI—helping them reach a $60M series B.On today's episode, Alex and Hector go behind the scenes to uncover:What it’s like to join a company in scale modeHow to move upmarket in the developer tech spaceHow selling to developers changed in 2023How to enable a great remote sales culture

Jason Fishkind recounts Sprinklr's sales journey from $5m to $500M in ARR.Sprinklr is one of the biggest names in social media management, but it didn't start out that way.As Sprinklr's first AE, Jason Fishkind helped the company 100x their growth from $5M to $500M ARR -- accelerating them through their IPO and earning a valuation of over $4 billion.On today's episode, Jason joins us to talk about a decade of sales growth at Sprinklr, including:What it was like to sell social media in the early daysCharacteristics of a successful sellerHow he kept up with Sprinklr’s growthTips for selling enterprise AI tools

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