Grow & Tell

Derek Osgood, Founder & CEO of Ignition, shares product marketing lessons from leading 9 major launches at PlayStation, reinventing a software category at Rippling, and founding Ignition—a product management platform.Derek Osgood is a career product marketer turned founder.He's made a career out of leading product launches at PlayStation and Rippling before founding Ignition, a go-to-market platform designed to help businesses launch products.In today’s show, Derek joins Alex to talk about:how his PlayStation game launch experience lends itself to SaaShow Rippling thought about reinventing a product categorytransitioning to the role of founder at his own companyhis best practices for a successful product launch

Jen Igartua, CEO at Go Nimbly, shares what she's learned in her 8 years of building a service-based business, plus tons of advice for RevOps teams.Jen Igartua, CEO of Go Nimbly, joins Alex on this week's episode to talk all things RevOps.First she uncovers what went into building her RevOps consultancy, including how they developed their service offerings, how they stay profitable, and how they recruit talent.Then, Jen and Alex dive deep into RevOps, where Jen shares tips on building a RevOps roadmap, structuring a RevOps team, and picking your tool stack.

Casey Armstrong, CMO of ShipBob, shares marketing lessons from his 5 years growing ShipBob to a $1b valuation. Casey Armstrong knows his way around ecommerce marketing – he's led both B2B and B2C marketing teams during his career.On this week's episode, Alex and Casey go deep on ShipBob’s startup marketing strategy, including:Why they started with only a few channelsCasey's advice for partnering with bigger brandsHow they built out their marketing teamHow their messaging has evolved with their ICP

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