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 led him to a career in revenue operations, he’s held sales & RevOps leadership roles at companies like Yammer, SalesLoft, and LeanData.
This week, Don joins Alex to share his greatest hits, including:
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 Global VP of Creative, she led a team that created over 3,000 branded content campaigns, earning hundreds of billions of views, over $100M in revenue for BuzzFeed, and a spot on Forbes’ 30 Under 30.
As ClickUp's CCO, Melissa grew their ARR from $2 to $200M in 4 years and ran some memorable billboard campaigns.
On today’s episode, Melissa breaks down the most memorable stories from her career, including:
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 down her advice for aspiring sales leaders, and her biggest tips for interactive demos that convert.
Catie also takes us through pivotal moments in her career, including:
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 habits that scale.
She joined Alex to discuss the psychology and strategy behind CS, including:
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 focusing on the customer.
This week, Wynne joins Alex to discuss her career journey, including:
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:
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:
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:
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:
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:
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:
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:
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
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:
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:
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:
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:
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:
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: