Don Otvos, RevOps leader and current GTM Strategist and Platform Evangelist at Chili Piper, shares the story of how one difficult conversation with a former boss made him switch career tracks after 20 years in sales. Since then, he has networked his way to a successful RevOps leadership career at companies like Yammer, SalesLoft, and LeanData. Don Otvos has built an entire career in RevOps off the back of thoughtful networking and product evangelism. After an honest conversation with a manager l...
Jan 13, 2025•50 min•Ep. 41
Melissa Rosenthal's first job out of college was as an intern at BuzzFeed. In her 6 years with the company, she rose to Global VP of Creative, delivering more than $50M in native ad revenue and $100M in branded content. She also helped ClickUp 100X their revenue growth as their Chief Creative Officer. Today, she's the co-founder of Outlever, a new startup that helps companies become the #1 news source in their industry. For our 40th episode, we’re talking to Melissa Rosenthal. As BuzzFeed’s Glob...
Dec 10, 2024•46 min•Ep. 40
Catie Ivey is the Chief Revenue Officer at Walnut — a leader in interactive demo platforms. Catie has built a standout career in sales, leading teams at some of the biggest names in marketing tech, including Marketo, Demandbase, and Pendo. Today, we’re taking a journey through pivotal moments in Catie’s career that shaped her approach to sales leadership. Catie Ivey has built a dream career in sales, leading teams at some of the biggest names in marketing tech. Today, she's joining Alex to break...
Nov 25, 2024•49 min•Ep. 39
Nobody prepares you for the jump from CSM to CS leader. But Rachel Provan is trying to change that. Rachel is a customer success leadership coach, helping CS leaders and early-stage companies build customer success strategies and leadership habits that scale. Nobody prepares you for the jump from CSM to CS leader. But Rachel Provan is trying to change that. Rachel is a customer success leadership coach, helping CS leaders and early-stage companies build customer success strategies and leadership...
Nov 11, 2024•41 min•Ep. 38
Most of our guests are builders, but Wynne Brown is a fixer. Learn how she's slashed churn, expanded renewals, and professionalized Sales and CS teams at Monster, GitHub, Seal Software/Docusign, Fable, RocketReach, and more. Wynne Brown spent the last two decades coming into scaling companies with leaky revenue — where she rights the ship, and then moves on to the next challenge. She’s revamped Sales and Customer Success at companies like Monster, GitHub, Fable, and RocketReach - mostly by focus...
Oct 28, 2024•44 min•Ep. 37
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 seller Why coaching sales reps is more li...
Oct 14, 2024•35 min•Ep. 36
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 piv...
Sep 30, 2024•52 min•Ep. 35
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 structured the relat...
Sep 16, 2024•47 min•Ep. 34
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 Animalz Her advice f...
Jun 24, 2024•45 min•Ep. 33
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 pr...
Jun 10, 2024•50 min•Ep. 32
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 abou...
May 27, 2024•52 min•Ep. 31
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...
May 13, 2024•52 min•Ep. 30
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 partnering with bigger brands How they built out their marketing team How their messaging has evolved with th...
Apr 29, 2024•48 min•Ep. 29
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 transition into an enterprise role The transition from managing reps to managing managers How to hi...
Apr 15, 2024•48 min•Ep. 28
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 ma...
Apr 01, 2024•52 min•Ep. 27
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, Lis...
Mar 25, 2024•45 min•Ep. 26
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 Yelp Yelp’s intense sales training program How they built a community marketpl...
Mar 04, 2024•48 min•Ep. 25
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 ...
Feb 05, 2024•48 min•Ep. 24
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—help...
Jan 29, 2024•50 min•Ep. 23
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 ea...
Jan 22, 2024•46 min•Ep. 22
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 ...
Jan 15, 2024•43 min•Ep. 21
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 mar...
Jan 08, 2024•42 min•Ep. 20
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 c...
Nov 27, 2023•50 min•Ep. 19
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 t...
Nov 13, 2023•47 min•Ep. 18
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 program Selling to open-source users at Confluent Early growth lessons from Column Sca...
Oct 23, 2023•48 min•Ep. 17
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 le...
Oct 10, 2023•44 min•Ep. 16
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 bootstra...
Oct 02, 2023•52 min•Ep. 15
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 past founder-led sales Democratizing sales metrics at Atrium The datafication of sales Building the...
Sep 25, 2023•53 min•Ep. 14
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 week's episode, Alex and Camille discuss: Positioning Notion as a broad product for B2B & B2C Build...
Sep 18, 2023•52 min•Ep. 13
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 comScore Going on a customer listening tour at Talkdesk to crea...
Sep 11, 2023•49 min•Ep. 12
