Shows
PIPs & PivotsBouncing back from being let go with Dustin BrownIn part 2 of my talk with Dustin Brown, he shares that he was let go for performance TWICE!This blew my mind because the Dustin I know closes 7 figure deals with the biggest brands in the world.We talk a lot about mindset and what kept him going when most reps in his shoes would have sought out another line of work.Connect With Dustin on Linkedin: https://www.linkedin.com/in/dustingbrown/Download all of the free stuff...2025-05-0436 min
PIPs & PivotsFrom the boiler room to closing 7 figure SaaS deals with Dustin BrownDustin Brown and I had really similar starts in sales.Dustin was able to go from jamming out 100 dials a day in a boiler room to closing 7 figure deals and earning life changing commissions.I had to get him on to learn how he's been able to put a career like that together.Connect with Dustin on Linkedin: https://www.linkedin.com/in/dustingbrown/Hit my website for free resources: www.dankow.skiElevate...2025-04-2735 min
PIPs & PivotsThe Pros and Cons of being a CSM, and balancing motherhood and a career with Val Walker, former AE. Pt.2Pt. with Val Walker where we talk more about her pivot from AE to CSM, and also some of the unique challenges of balancing a career in tech with motherhood. She has two boys under 6 and if you know anything about boys that age, you know it's chaos.
Val and I worked together as founding AEs at Evernote. After I left there for Outreach, the whole team was RIF'd while she was on maternity leave. She used that as an opportunity to pivot into Customer Success and hasn't looked back. This is a great...2025-04-2027 min
PIPs & PivotsPivoting from sales to Customer Success with Val Walker. Pt.1Val and I worked together as founding AEs at Evernote.
After I left there for Outreach, the whole team was RIF'd while she was on maternity leave.
She used that as an opportunity to pivot into Customer Success and hasn't looked back.
This is a great episode for anyone considering a move into CS.
Connect with Val: https://www.linkedin.com/in/valrwalker/
For my career course, free resources, and to work with me, visit www.dankow.ski
Connect with me on:
...2025-04-1324 min
PIPs & PivotsCreating a vision for your career to keep you out of bad roles and companies. Career strategy for BDRs and AEsIn this solo episode I talk about not just the importance of having specific career goals, but also a framework for coming up with one that's sure to propel you towards success.
For my career course, free resources, and to work with me, visit www.dankow.skiConnect with me on:Linkedin - https://www.linkedin.com/in/chrisdankowski/Twitter - https://x.com/cdankowski2025-04-0620 min
PIPs & PivotsPivoting from sales to Sales Operations with Laura Flores. Pt. 2Pt. 2 with Laura Flores
Laura and I worked together way back when I first moved to Austin over 11 years ago.
She was a freaking blast to work with, and was always someone who I couldn’t help but to root for.
I watched her get hired at Oracle, move from BDR to AE, AE to Sales Manager, and then go work at Salesforce as an AE.
She went through a debilitating burnout triggered by a loss in her family th...2025-03-3032 min
PIPs & PivotsBurning out and pivoting out of sales with former Enerprise AE Laura Flores. Pt.1Laura and I worked together way back when I first moved to Austin over 11 years ago.
She was a freaking blast to work with, and was always someone who I couldn’t help but to root for.
I watched her get hired at Oracle, move from BDR to AE, AE to Sales Manager, and then go work at Salesforce as an AE.
She went through a debilitating burnout triggered by a loss in her family that led to her leaving sales without a plan....2025-03-2336 min
PIPs & PivotsEntreprenuership and Sales Leadership with former BDR Chris Cicconi. Pt.2Chris Cicconi Pt. 2Chris and I initially crossed paths while he was leading the BDR org at Visier and I was working at a sales consultancy.I wanted to talk to him to uncover what types of reps make the best BDR Managers, and how an individual contributor can start preparing for a career in management right now.Chris's story is also one of career pivots and entrepreneurship and he shares some great insights on each.
Connect w/ Chris Cicconi:https://983media.com/salesunicrn.comhttps://www.linkedin.com/in...2025-03-1635 min
PIPs & PivotsFrom BDR to Sales Leader with Chris Cicconi. Pt.1Chris and I initially crossed paths while he was leading the BDR org at Visier and I was working at a sales consultancy.
I wanted to talk to him to uncover what types of reps make the best BDR Managers, and how an individual contributor can start preparing for a career in management right now.
Chris's story is also one of career pivots and entrepreneurship and he shares some great insights on each.
Connect w/ Chris Cicconi:
https://983media.com/
...2025-03-0927 min
PIPs & PivotsSelf care for sales reps. Pt. 2 with current Burnout Coach and former sales rep Emily JohnsonPt. 2 with Emily Johnson
Emily Johnson has been helping women avoid, treat, and recover from burnout for the past 4+ years.
She comes from a sales background and talks about some of the common sales stressors that led to her burnout, how she recovered, and how she came to dedicate her life to helping others.
I was really curious to learn WTF burnout is exactly, where it comes from, what it does to us, and how to manage it.
Connect...2025-03-0214 min
PIPs & PivotsMaking the move from IC to Sales Leader with Scott Leese. part 2 of 2Scott Leese has promoted more people than he can count from IC to manager, and many of those people are now VPs, CROs, CEOs, and founders.I wanted to know what he would tell a current BDR or AE who wants a career in sales leadership, what they should be doing now to prepare for that move.He shares some great actionable insights that you can implement today to put yourself in a position to elevate your career.To connect with Scott, reach out...2025-02-2631 min
PIPs & PivotsBurning out and recovering. Pt.1 with Burnout Coach and former sales rep Emily JohnsonEmily Johnson has been helping women avoid, treat, and recover from burnout for the past 4+ years.She comes from a sales background and talks about some of the common sales stressors that led to her burnout, how she recovered, and how she came to dedicate her life to helping others.I was really curious to learn WTF burnout is exactly, where it comes from, what it does to us, and how to manage it.
Connect with Emily:alignwithemilyj.com/ https://www.linkedin.com/in/emily-johnson111392/
For my career course...2025-02-2321 min
PIPs & PivotsFinding your niche in sales with Scott Leese. Part 1 of 2There's this thing in sales where most reps just default to a career strategy of BDR to AE to Manager to Director to VP, without ever stopping to think if that suites them or not.I'm of the opinion that you should figure out your ideal role/segment/buyer persona, etc and go all in on that particular niche.Scott is of the same mindset, and we unpack all that's involved in a career strategy like that.We also spent some time talking mindset...2025-02-1930 min
PIPs & PivotsCrushing as an AE from 9-5, and selling your startup after hours. Pt. 2 with former AE and current CEO Troy MunsonPt. 2 with Troy Monson, the CEO of Dimmo...Troy Monson has always been a hustler. From selling snacks at construction sites as a kid, to selling side hustle SaaS projects while working as a full-time AE.We talk about what goes into being a high performer from 9-5, while also moonlighting as a founder.We cover time management, work-life balance, and we talk about how Troy knew when it was time to move on from 9-5 work and go all in on Dimmo.
Connect with Troy!https://dimmo.ai/https...2025-02-1626 min
Sales PlayersWinning an Electric Car as a Sales Spiff and Other Crazy Career Stories with Chris DankowskiChris Dankowski is a Sales Strategy Consultant and Coach to Sellers and Founders in tech. Based in Austin, Texas, Chris has previously sold at top companies like: Evernote, Outreach and HubSpot. In this episode, Chris shares insights on managing your tech sales career.SPONSORS:• Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodburyEPISODE LINKS: • Connect with Chris: https://www.linkedin.com/in/chrisdankowski/ • Website: https://www.dankow.ski/CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • ...2025-02-1255 min
PIPs & PivotsBuilding successful startups while carrying a bag. Pt.1 with former AE and current CEO Troy MunsonTroy Monson has always been a hustler.
From selling snacks at construction sites as a kid, to selling side hustle SaaS projects while working as a full-time AE.
We talk about what goes into being a high performer from 9-5, while also moonlighting as a founder.
We cover time management, work-life balance, and we talk about how Troy knew when it was time to move on from 9-5 work and go all in on Dimmo.
Connect with Troy!
https://dimmo.ai/
https://www.linkedin...2025-02-0924 min
PIPs & PivotsBDR Contract Stacking to unlock freedom and increased income as a BDR. Pt. 2 with BDR turned Enterprise AE Fidel Cache FlowPt. 2 of my talk with Fidel Cache Flow.Fidel Cache Flow is a huge influencer on sales Twitter and a real mystery man.
He worked his way through school as a BDR and his currently an Enterprise AE at a big F500.
His Desperado Sales Group is a wildly successful community that, among other things, enables BDRs to operate as hired guns via contract stacking.
Tune in for his story and to learn more about contract stacking.
https://x.com/FidelCacheFlow2025-02-0229 min
PIPs & PivotsBDR Contract Stacking and being your own boss as a BDR. Pt. 1 with BDR turned AE Fidel Cache FlowFidel Cache Flow is a huge influencer on sales Twitter and a real mystery man.
He worked his way through school as a BDR and his currently an Enterprise AE at a big F500.
His Desperado Sales Group is a wildly successful community that, among other things, enables BDRs to operate as hired guns via contract stacking.
Tune in for his story and to learn more about contract stacking.
Connect w/ Fidel:
https://x.com/FidelCacheFlow
https://fidelcacheflow.io/
...2025-01-2626 min
PIPs & PivotsMoving into sales management. Pt. 2 with BDR turned Sales Leader Caroline MaloneyPt. 2 with Caroline MaloneyCaroline (friends call her Carole) and I are cut from the same cloth in that we’re curious people who go all in on their curiosities.We had a great talk about what led her into BDR leadership, then to Sales Enablement, and back into sales leadership.We chatted about the perception vs. reality of “job hopping” in sales. I have some strong opinions on the matter that I shared.I was very intentional in asking her what types of sales reps make the best sales enablement people and sales managers, and ho...2025-01-1932 min
PIPs & PivotsFrom BDR to Manager to Sales Enablement. Pt.1 with BDR turned Enabler turned Sales Leader Caroline MaloneyCaroline (friends call her Carole) and I are cut from the same cloth in that we’re curious people who go all in on their curiosities.
We had a great talk about what led her into BDR leadership, then to Sales Enablement, and back into sales leadership.
We chatted about the perception vs. reality of “job hopping” in sales. I have some strong opinions on the matter that I shared.
I was very intentional in asking her what types of sales reps make the best sales enablement people and sales manage...2025-01-1232 min
Cold Outreach PodcastLost Everything in 2008—Now a SalesLoft Pro Shares Cold Outreach Secrets (plus his AI predictions)Mastering Sales: Chris Dankowski's Guide to Transformative Cold OutreachJoin us as we dive deep with Chris Dankowski, an award-winning sales strategist at Sales Loft and alumni of Evernote, Outreach, and HubSpot. In this episode, Chris unravels his remarkable career journey—from losing everything in the 2008 crash to excelling in sales for top industry brands. Learn how Chris used cold outreach to change his life and discover strategies for navigating job markets, personalizing cold outreach, and leveraging AI in sales. Whether you are a BDR, AE, or someone looking to break into a top-tier organization, this episode is...2024-12-1959 min
PIPs & PivotsMissing quota - managing the mental gameAccording to Repvue, most sales reps are falling short of quota. What can you do to mitigate stress when the game is set up for you to fail?
That's the topic.
Checkout my site for more!2024-08-2914 minPIPs & PivotsMiddle of the mall to enterprise SaaS salesCharlie Cruz is an awesome dude with an awesome career story.
He started out selling cell phones in a mall kiosk and worked his way up to becoming an Enterprise AE.
How the heck did he do that!?!?!
You've got to listen to find out :-)
Connect with Charlie on Linkedin
Free Resources, etc2024-08-1328 minPIPs & PivotsSoooo much sales advice! How to tell what's useful.Solo episode where I provide a framework you can use to cut through the mass amounts of sales content to determine what's useful to you, and what doesn't apply.
https://amzn.to/3LE3gOI2024-07-2425 minPIPs & PivotsWorking through unprecedented times... againThe “unprecedented times” really don’t stop, do they?
Does anyone else find it jarring how little major traumatic events are even acknowledged in our 9-5 dealings?
Like, we’re all just disassociating from the persistent terror that our country could spontaneously combust at any second.
School shootings, political violence, police brutality, class conflict, funding a genocide with our tax dollars, and bigotry of every variety… all part of what passes for normal for us.
How many of us have dissociated as a survival instinct because living in reality and being able to fu...2024-07-1612 minPIPs & PivotsAI can replace youAI is going to replace a lot of sales reps.
Not all, but a lot.
It's going to happen fast, too. Like within 3 years or so, IMO.
It's the transactional roles that are going to suffer in SaaS sales.
More traditional industries that are slower to adopt new tech will still employ these folks, so it's not like they'll be jobless. However, they won't make the same money they do now.
Strategic sellers will be safe, but they'll need to adapt a bit.
In this episode, I lay out exactly what you should do today to safeguard yourself from being...2024-07-0343 minPIPs & PivotsIf I could do it all over again...Having been out of sales for 3+ years now, I've had space to reflect on what I could've/should've/would've done differently as an AE.
That's what I cover in this episode.
https://linktr.ee/cdankowski
2024-06-2626 minPIPs & PivotsNikki Ivey - How heavy is your knapsack?Black women are 7.7% of the total U.S. population but only make up 3% of tech workers.
Women of color are 65% more likely to be laid off than men.
Less than 1% of Fortune 500 CEOs are women of color.
64% of new women-owned business are started by those of color.
Nikki Ivey's experience as a black woman working in tech, and specifically her work in DEI in the tech space, helps to shed light on why these numbers are what they are and what can be done to change them.
Connect with her on LinkedIn
See her at Women Consulting Corporate LIVE
July 25...2024-06-051h 14PIPs & PivotsGetting hired with Destiny BrandtDestiny Brandt's agency, It's Destiny Recruiting, just celebrated 4 years in business!
Their specialty is placing sales reps and execs into highly sought-after roles in tech and beyond.
In this episode, she shares all the do's and don'ts of getting hired.
Her links:
https://topmate.io/destiny_brandt
https://www.itsdestinyrecruiting.com/
My links: https://linktr.ee/cdankowski2024-05-291h 02PIPs & PivotsAvoiding burnoutWhat do you do when you can feel burnout creeping over you?
https://linktr.ee/cdankowski2024-05-2228 minPIPs & PivotsBreaking into enterprise sales with Jesse WoodburyJesse Woodbury is an Enterprise AE and host of the podcast Sales Players.
When he and I worked together he was pumping out 100 dials a day for not a lot of money.
Flash forward 10 years and he's cashing six figure commission checks.
The interview focuses on how he got from A to B, and how how can do the same.
Connect with him on LinkedIn and at JesseWoodbury.com as well as his Sales Players podcast.
You can find me all over the place via https://linktr.ee/cdankowski2024-05-1558 minPIPs & PivotsProspecting into your dream jobFind an awesome role on LinkedIn?
How are you going to make sure your resume is seen?
https://linktr.ee/cdankowski
2024-05-1012 minSales PlayersHow to Find the Right Path in Your Sales Career with Chris DankowskiChris Dankowski is a Revenue Strategist at Salesloft by day. Career Advisor for sales reps by night. - Former AE at top companies such as: Evernote, HubSpot, and Outreach. Today Chris shares insights on Sales careers from landing a role at a top tech company to pivoting out of sales into another role.
SPONSORS:
• Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com/?kfl_ln=jesse-woodbury use this link with promo code JWSURFE5 for a 5% discount on your first year
• Apollo (Find, contact, and close your ideal buyers) - http...2023-05-3158 min
Sales PlayersFrom Bankrupt Small Business Owner to Top SaaS Seller with Chris Dankowski of Sapper ConsultingChris Dankowski of Sapper Consulting shares his career journey from small, bankrupt business owner to SaaS AE at some of the industries top companies. Chris also digs into insights around effective prospecting & shares how to land great opportunities in SaaS. SPONSORS: • Surfe (Connect your CRM with LinkedIn in 60 seconds) - https://www.surfe.com?fpr=ssp use this link with promo code JWSURFE5 for a 5% discount on your first year • Close (The CRM Built for Growth) - https://refer.close.com/sspEPISODE LINKS: • https://www.linkedin.com/in/chrisda...2021-11-1757 min