Share
))
HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
…
continue reading
Manage episode 521497778 series 3694238
Content provided by Syed Asad. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Syed Asad or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.
Most people think you need to job hop every 18 months to climb the ladder in tech. Margaret Sikora proved them wrong.She started at Woodpecker in 2017 as a junior customer success agent answering support tickets. Eight years later, she's the CEO. Same company. No shortcuts.Junior CS → Customer Success Officer → Head of Support → Head of Product → COO → CEO.She didn't parachute in from Google. She didn't get an MBA. She just kept proving she could do the next thing. Oh, and she got a PhD in law along the way (which she admits was mostly pointless).This is the most honest conversation I've had about what it actually takes to go from entry-level to CEO in B2B SaaS.
Most people think you need to job hop every 18 months to climb the ladder in tech. Margaret Sikora proved them wrong.She started at Woodpecker in 2017 as a junior customer success agent answering support tickets. Eight years later, she's the CEO. Same company. No shortcuts.Junior CS → Customer Success Officer → Head of Support → Head of Product → COO → CEO.She didn't parachute in from Google. She didn't get an MBA. She just kept proving she could do the next thing. Oh, and she got a PhD in law along the way (which she admits was mostly pointless).This is the most honest conversation I've had about what it actually takes to go from entry-level to CEO in B2B SaaS.WHAT WE COVER:- Why most customer success people burn out (and how she avoided it)- The exact moment she realized she could transition from CS to Product- How to manage people who used to be your peers without it getting weird- Why she got a PhD while scaling to CEO (spoiler: prestige is fake)- The hardest decision she made as CEO (withdrawing products her team built)- Is it actually lonely at the top? Her honest answer- Why "follow your passion" is garbage advice (discipline beats motivation)- The one skill every CEO needs that no one talks about- How Woodpecker competes in a crowded cold email market (Lemlist, -Instantly, Smartlead)- Her take on whether cold emailing is dead in 2025- What changes when you become CEO (and what doesn't)- How she avoids burnout as CEO (or doesn't - her answer surprised me)If you're in customer success, product, sales, or any GTM role and you're wondering how to build a real career without job hopping every year, this is for you.Margaret doesn't do corporate speak. She's brutally honest about imposter syndrome, making decisions that piss people off, and why being CEO is exhausting but worth it.
38 episodes
