Grow & Tell

Chris Michelmore, Head of Mid Market Acquisition at Zoom, tells the nine-year story of how he ascended from first-time SDR to senior sales leader.It's rare for a first-time SDR to stick around long enough to become a sales leader at that same company.But that's exactly how Chris Michelmore became the Head of Mid Market Acquisition at Zoom.This week, he's taking Alex through his journey up the company ladder, including:What made him so successful as a sellerWhy coaching sales reps is more like selling than you'd thinkThe big differences between leading sales directors vs. AEsWhat it’s like growing alongside a company in hypergrowth

10-14

34:51

Matt Green, Co-Founder and CRO of Sales Assembly, shares the company's founding story, the keys to a great sales training program, plus the biggest sales skills most teams are missing today.Some of today's best companies started over a cup of coffee.That's how Matt Green and his co-founder, Jeff Rosset, started Sales Assembly – the go-to sales resource for some of the world's best B2B tech companies.Matt joins Alex this week to share the growth story of Sales Assembly, including:why they pivoted from role-backed to skill-based trainingwhat today's most successful sales leaders are talking aboutthe 2 biggest skills that sales teams are missingthe most common struggles he sees with new sales leadershis advice for selling through champions

09-30

51:59

Monica Perez, Head of Customer Success at Notion, shares the four-year journey of building Notion's foundational CS team.Customer Success at a product-led company is a completely different animal.When Monica Perez was brought in to grow Notion's foundational customer success team, they were already at $40 million in revenue.Today, Monica joins Alex to discuss what it was like to build a CS program on top of a strong PLG engine — including:how their customer onboarding is structuredthe relationship between sales and CShow they mature customer accounts over timehow they measure the success of their CS programs

09-16

47:15

Devin Bramhall, growth advisor and former CEO of Animalz—the content marketing agency for companies like Amazon, Google, and Intercom—shares candid stories about 3xing the agency's revenue to $11.5M in only 2 years.Devin Bramhall is a content marketing legend.After 3xing revenue to $11.5M in only 2 years at Animalz, she went on to build a successful consulting biz while growing her marketing podcast, Don't Say Content.This week, Devin joins Alex to discuss:How she scaled AnimalzHer advice for startups thinking about contentHow she grew her podcast

06-24

44:59

Eloise (Shuttleworth) Salisbury, newly named Chief Customer Officer at AutogenAI, recounts lessons from 5 years of building Iterable's customer success program from the ground up, how she's approaching her first 90 days in a new CS leadership role, and why she founded Women in SaaS.What does it take to build an enterprise-level customer success program?Eloise Salisbury, Chief Customer Officer at AutogenAI, joins us this week to break down what she learned scaling Iterable's customer success program.Eloise joined Iterable, a cross-channel marketing enablement platform, after their Series B. In her five years with the company, she scaled their CS to an international audience, introduced an enterprise CS and implementation track, which ultimately helped the company grow to a $2 billion valuation.In today’s episode, Alex and Eloise discuss:how to build mid-market and enterprise CS teamswhat makes an ideal CS/sales relationshiphow she's approaching the first 90 days at AutogenAIwhy she founded Women in Saas (and her advice for women in tech leadership)

06-10

50:04

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

05-27

51:42

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.

05-13

52:07

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

04-29

47:44

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

04-15

48:22

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

04-01

51:54

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

03-25

44:46

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

03-04

48:28

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 their point-of-sale products.In today's episode, Kyle joins Alex to discuss:Building 3 sales motions from scratch at LeagueWhy he made the move from startups to ShopifyShopify's POV sales pitchWorking with a first-time founder at Owner

02-05

48:05

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