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...

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...

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 channels Casey's advice for partneri...

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 about Productboard's early product-led sales process What it was like to...

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 runn...

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...

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...

Kyle Norton, CRO of Owner, shares learnings from launching Shopify's retail POS program and building Owner's sales team. Kyle Norton has led sales teams at two unicorn companies — League and Shopify. While leading sales at League, he grew revenue to $20 million and scaled their sales team to 40 reps. 3 years later, he joined Shopify as Head of Revenue for their retail division to help roll out the...

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 ove...

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 ab...

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 shak...

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...

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 e...

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 countin...

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...

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 s...

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 bo...

Peter Kazanjy, author of Founding Sales and co-founder of Atrium, shares sales advice for startup founders and early sales hires. Pete Kazanjy literally wrote the book on founder sales. As a three-time startup founder, Pete knows the ins and outs of building an early-stage sales team. On today's episode, Alex and Pete discuss: Pivoting his first startup to TalentBin Writing Founding Sales Evolving...

Camille Ricketts, former Head of Marketing at Notion, shares how Notion through community. You don’t go from unknown startup to household name without a great community strategy. That was definitely the driving factor behind Notion's growth. As the 11th hire and Head of Marketing at Notion, Camille Ricketts built the brand foundations that enabled Notion to take off like a rocket ship. On this wee...

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...

Marketing leader Maya Spivak shares what went into launching successful brand campaigns at Wealthfront and Segment. What goes into creating a tech brand that not only stands out but deeply resonates with its audience? Maya Spivak, an experienced brand and marketing expert, joins us in this episode to share her experience building TV and billboard campaigns for Wealthfront and Segment. In today's e...

Ben Solari, VP of Sales at Jellyfish, shares sales advice for taking technical products to market. If you’re not super technical, sales is a great way to get your foot in the door in the startup world. That’s how Alex (our host) got started at Yelp before eventually founding Dock. But what happens when you have to sell a very technical product to a very technical audience? Ben Solari joins us in t...

Alexa Grabell, Founder of Pocus, shares the company's founding story, plus lots of product-led growth advice for go-to-market teams. Pocus has ridden the PLG wave, earning $23 million in funding and landing big-name SaaS customers like Webflow, Loom, and Miro only two years since its founding. In today’s episode, Alex and Alexa discuss: The backstory behind Pocus's founding Pocus's approach to fun...

Bryan Rutcofsky, Co-Founder and CRO of Marqii, shares how he grew sales at Yext to over 140 team members and $100 million in revenue. Inflated job titles are a bit of a cliche at startups. You see a lot of C-suite and VP-level roles that probably shouldn’t have been handed out. But when Bryan Rutcofsky grew sales at Yext to 140 team members and over $100 million in revenue, he certainly earned the...

Rich Liu, CRO of Everlaw, recounts stories from his time leading early sales at Facebook in 2010, taking the plunge into B2B SaaS at MuleSoft, and selling a corporate travel platform during the pandemic. Rich Liu’s philosophy to scaling sales at 5 unicorn companies has been surprisingly simple: build the sales process to help the customer achieve their business outcomes. In this episode, Alex and...