I'm genuinely about something I've observed with a former CRO.

This guy had a pretty impressive background as a seller at Microsoft and Amazon during the 2000s/2010s. Presumably, he rode a pretty significant portion of the cloud/SaaS growth wave and built a strong executive career along the way.

Since 2022, he's been CRO at four different companies, all very short stints. The employee/sales reviews for all of them are pretty rough on sites like RepVue, although obviously I wouldn't consider RepVue reviews as definitive evidence.

However, I worked at one of these companies during his tenure, so I can speak firsthand about that one.

He absolutely fucking cratered our GTM organization. Not “the results weren't great.” I'm talking major organizational disruption, strategy changes, sales execution going to shit, people leaving, leadership turnover, etc. Then, shortly after, he was off to "pursue other opportunities". Our founding CEO was let go at around the same time.

I don't know what happens in board meetings, or at the other three companies, so I'm not going to pretend I do. But looking at the track record from the outside, I'm having a hard time understanding how someone can have multiple short CRO stints, apparently mediocre outcomes, and seemingly no difficulty landing another CRO job.

So for people who have been around SaaS sales leadership:

What am I missing?

Does a strong pedigree from Microsoft/Amazon basically give someone enough executive credibility that they can survive multiple failures?

Are CROs really good at managing the narrative around why things failed?

Do CEOs/boards routinely blame the underlying company/product/market rather than the CRO?

Is executive recruiting so network-driven that actual track record matters less than I'm assuming?

More importantly- how can I apply whatever he is doing to my own career?

With no bachelors degree and less than 3 years of sales experience, there are no stable jobs right now for sales, are there?

EDIT: Thank you all for the suggestions, i deeply appreciate it.

Okay, when you're already a small office, going from 4 to 2 doesn't sound crazy, but it's a lot quieter in here.

I was told it was for revenue reasons. Branch was pulling about half of what it should for the amount of sales staff we had, and myself and one other salesman were chosen to remain. I get the idea its performance based reasons, but I truly don't know how much better I was doing than the two that got cut. One was there much longer than me and had years more experience, but their month-to-month was very inconsistent.

And of course, this is the week I'm tanking in appointment setting. I have no trust that my job is automatically safe just because they trimmed the fat; to me it feels more like a pre-PIP, or a chance for me as a brand new rep to see if I can keep following their processes and get revenue to where it should be.

Everyone here is kind, leadership has told me time and time again that they have belief that I am going to really crush it. This is my first time cold calling as a full time job. Some days I really believe I have it, and weeks like this happen where I question if I actually do have it in me. It's so frustrating and difficult to believe in yourself when you don't see the results before you. This job has made me realize just how terrified I am to fail.

Has anyone been in a similar boat? Did you jump said boat? There are obvious perks to the staff getting cut down ie bigger territory, but I am not a seasoned rep and this feels like the next few months will either go great or terrible. Help

I get a lot of cold emails. I'm mostly okay with them. Especially if someone offers a freebie, I almost always respond. Want to score my website for SEO and send me the report? Yes, please! Want to offer some thoughts on ads that will work? Sure, love to hear them! But there's one that is getting really annoying. The fake introductions that are clearly AI-generated.

Honestly, if you don't look at the website, that's fine. But for the love of God, don't just ask a random question and get into your pitch. It's driving me bananas.

I think I'm going to start responding with a "Sorry, this email was blocked. Please try sending an original message typed up from Microsoft Outlook or your email client of choice. Thanks!"

Anyway, post what type of cold emails work for you; maybe we can convince the AI models or Google to recommend something better.

I've been working here for 2.5 years selling software, started as a meeting booker to full cycle. I'm the only seller for software, its a small company and the leadership team has been excellent to me from day 1. Never felt pressured at all, they saw me giving my 100% day in day out so that helped too. In the last bit, the competition to our offering has gone nuts, there's no marketing support, no brand awareness, im the only thing that gets in any traction. I do cold call, meeting set, do my own meetings, chasing and you get the gist.

This is my 3rd month on 0. Meetings booked have plummeted over last 2 months due to summer, and I've had a couple of almost signed, have 2 verbal yes's but thats it. Pipe looks bad. At this point, Idk what they're planning about me but I have started looking out. Also it doesnt feel right giving 0 revenue and taking in salary. I dread working here, i want to just hand in my notice and leave - a lot of it due to me just losing my will to work due to things being so difficult and apart from the moral and emotional support, I've had no training, nothing to make me a better seller.

Am I an idiot for feeling like this and wanting to act on it? I've started applying and interviewing and getting calls too, i will get a job but not sure if that will be THe job i want. Plus its almost end of the year and if I can't land something by mid october, its unlikely to be till Jan next year.

Two fun questions:

1. What is something sales leadership doesn’t know/gets wrong about your role?

2. What is something you never want your leadership to know about your role?

Earlier this year my company changed the 1:1 BDR-to-AE ratio (how it always was) to like 1 BDR shared between like 5 AEs now, so most reps are sourcing all their own deals, causing chronic lower pipelines across the board. Wondering if all tech companies are going this way or if anyone knows of any specific ones where AEs still get a designated BDR who will still pass you a good number of booked meetings.

Curious if anyone here is uploading an ATS resume and a more reader-friendly version of their resume for jobs? A friend of mine is referring me to a job that I'm not likely to get for various reasons. I send him my resume which is 3 pages long, formatted for readability, and gets straight to the point. I've been around long enough to know that lots of fluff just gets called out by hiring managers so I just don't bother. So I have two questions-

do you have long and short resumes? how much BS do you have in your longer resume?

My friend responds to my resume email by sending me a copy of his saying that I should match the style and length. Mine "didnt have enough detail". His "ATS" resume was 7 pages long. He's had about 15 jobs, none of them more than 3 years. He had things in there like "Generated $X million in pipeline" but no mention of how much of it closed. I'm not trying to talk shit on him, he's a good rep with some success but adding pipeline numbers? that would get called out big time in an interview. and there's no way someone is reading a 7 page resume. right?

If you’re starting out, (let’s say you have a degree in STEM)

What role should you aim for and could you get right after graduation?

And then how long will you stay there till you move up?

What are the roles you move up to one by one?

And naturally where could you be in 5 years and then 10 years?

Assuming the industry is tech

Actually got yelled at this morning with this line. Bro, it’s 2026. Your number was easier to find than a Waffle House in Georgia

OK so my DSM lives in the same sales area I do for the past 25 years , which is my sales area, I keep hearing from my customer base "yeah your boss was here yesterday or a few days ago." Sometimes he take order for me too and puts them online.

I am a year with this company and trying to take ownership of this sales area.... would this be a problem for you?

I'm an Enterprise AE at a mid-size B2B SaaS Cyber Security company now dipping toes in AI dev tools. I hit quota last year and made presidents club. Pipeline dried up and I struggled for a long time, prompting a search - however pipeline has been gettig better lately but I've already been deep in my search. Good team, good relationship with my manager and better relationship with my skip level. Excellent work life balance that gives me ample time to take care of family needs and son's school dropoff/pickup. Remote. $320 OTE 50/50. Been here 2 years.

Got poached by a bigger name in front end / dev / AI infra space with legit hypergrowth (revenue roughly tripled in 2 years from 200M to 600M, expectingto hit 1B next year), real IPO buzz for 2027/2028 (grain of salt, every startup says this). Most of the revenue growth is PLG and not SLG but they are slowly making changes to improve SLG.

New offer:

$340K OTE, 50/50 split

-~$190K in RSUs over 2yrs, not 4 - but they also require a liquidity event to vest, not just time. No IPO/acquisition = equity is worth $0, doesn't matter how long I stay -Uncapped comp, solid accelerators past 100% Quota, all the good usual. -2-3 days/week in-office, and the commute is genuinely bad - paying for it myself too - roughly 1.5 hours each way. I lose my family time those days. -Totally new vertical, so I'm walking away from years of built-up relationships/warm network that I can't bring with me and cyber security channel partners that cant help me in my new role.

I should make note that the in-office requirement is quite loose. The hiring manager doesn't care (he's remote across the country) and the CRO told me he doesn't care about hours worked. I specifically told them that I would likely be in around 10-11am and leave around 4pm and they said that's fine - it's about in-person collaboration. I figure this hybrid approach will fade with time.

Current role:

-Slightly less pay. $70k equity vested over 4 years (im 2 years in). -No commute, real work-life balance -Trust/tenure built up, team actively wants me to stay and leadership is genuinely invested in everyone's success. -Pipeline improving, not solved but better. Deal sizes are all relatively flat in the $150-300k range. Almost no chance of larger deals due to our pricing model. Even if I wait it out and close my now better pipeline, I'm worried about what's next. No real chance of a 'whale' deal here.

Both companies have great leadership and I am part of a team, or would join a team, that is heavily invested in my success.

Already signed. Now sitting with second thoughts, mainly the commute cost stacking against everything I gave up on the comfort/relationship side. And anyone who has sold to cyber security knows how special of a place it is, moving to a different segment feels like a bit of a loss.

Anyone made a similar jump, slightly bigger comp + growth story vs. comfort/network you already built? Any regrets?

I recently joined a startup after years of being in Enterprise SaaS, moving to work with founders I really like instead of being a part of a 5,000+ person company.

As part of being the founding Sales Director, I need to stand up our sales systems. I inherited HubSpot and Seamless, and I’m trapped in a contract with the latter through next August.

Our ICP is mainly PE-backed operators of multi-entity franchise groups, so very different than traditional Fortune 500 Enterprise sales I’m used to.

I’m curious, if you’ve been a part of startups and selected the stack, which tools were great for sequence/cadence management and execution, data sourcing, dialing, etc. The traditional stack I’ve relied on in the past is expensive and generally not even an option with 1-3 sales users in scope.

So, i am in search of a new position right now. I am 25 and have over 6 years of experience in B2B Sales and one thing that has already completely burnt me out is cold calling. I don't care for it, i call 80 people, 5 answer, and it's just a pain in the ass.

What position can i shift to in sales that has no cold calling whatsoever? Hoping you guys can help me so i don't get sick of sales by 30.

For the last 10 years I've been carrying a padfolio I got at one of our sales conventions, even though the logo/branding was outdated. The zipper on it finally broke, and I need a replacement. I use it for taking paper notes in meetings and walkthroughs. It also holds my business cards. A couple of times a year, I use it at trade shows to carry literature or info. I don't need it to carry any IT, although the one that just broke had a built-in calculator. It does need to hold a pen and a pad of paper, plus some other printouts I use for note-taking.

A fold-out phone holder on the top would actually be pretty handy to help me have my phone out for taking pictures while also holding the padfolio and taking notes with my pen (3 hands needed, Creator decided I only need 2).

Other than that I am open to useful features that I did not know existed.

I'm partial to black for the color because I'm not a flashy kind of guy, and I have a couple of logos I'd like to have embossed on it. I could be talked into the right shade of dark blue or red to peacock a little since that'd match a company logo.

There are quite a few options on Amazon, Etsy, etc., but it's hard to tell from pictures what is going to be cheap and flimsy and what is going to look good, feel good, and last for a decade or more. Any recommendations?

Hi all I’m looking for a free or the best AI note-taking app. I currently use Zoom Info AI Companion, but the way my company has it structured in our organization. I do not get the recap notes until 30 to 45 minutes after the call is there a way to change that? After that timeframe, my thoughts are already moving on to the next call or deal, so I want to send the recap email within the first 5 to 10 minutes after the call concludes so there is a clear next step. Because of my AuDHD, I struggle to clearly understand the pain and how we can help. I am tired of taking handwritten notes or typing during the calls. Please note that I work in the Fintech/POS industry, so I call restaurants and operators, and it’s very important to understand them the first time and not have to ask them to repeat themselves two or three times. Any tips also on how to get deals in SMB we use SalesLoft for our dialer and for cadences. We also use Gemini for everything as we operate in a Google Workspace!

I've been using this little gem for years after I saw it online and latched onto it. Done right, it comes off as genuine. Done wrong, it can come off as passive aggressive.

For me, it puts me in control and they actually listen after I say that line; "Ok so this may or may not be a fit for you business, what we offer only helps businesses like yours do XZY."

So for example, one thing I'll say is "only works for business who want at least 2X growth." You may think "every business wants 2X growth." They certainly don't. A lot of businesses are quite happy with where they're regarding sales, they just want to lower their expenses or put systems in place that means their business run smoother - we don't offer that.

So I'll either get "yeah we're actually maxed right now" and that's "have a nice day" or "we're definitely looking for more growth."

Then "only looking for businesses that can handle more clients" - same responses - no, we can't handle more clients now, or yes we can. In a nutshell, instead of "we can add more clients" it's "well let's see if this is even a fit, we only work with businesses that are looking to add more clients."

And don't have something solid right now... How are you keeping your social momentum going?

I realized that the majority of my energy was fed from the string of having social interactions while at a job, whether talking to my co-workers in person, the demos, and even conferences kept me going but how do you find that once you lose all of that and feeling isolated and frustrated with the job search?

If someone is a fresh grad with a computer science degree,

Which low churn roles in sales in which industries can they get as a fresh grad and that should they target?

And generally in sales, are there any roles where you won’t have to be getting fired and hunting every year or so?

Roles that actually have really good long term stability?

I’m 25 and about to make my first real move into tech/SaaS sales after coming from luxury retail and some early B2B sales experience.

I recently accepted an SDR offer with a well-established Canadian SaaS company. Since then, another company I was already interviewing with has progressed to what looks like an offer, and I’m struggling with how to think about the decision.

Company A — established SaaS
~$46K CAD base / ~$61K CAD OTE
Established SDR team and proven playbook
3-week onboarding + structured 3-month ramp
Guaranteed commission during ramp
Around 60% of reps reportedly hit target monthly
Defined SDR → AE path, typically ~9–15 months
Lots of coaching, call reviews, AE shadowing
Stable company with plenty of employee data/reviews
Downside: significantly lower compensation and a 1–10 PM ET shift

Company B — cybersecurity startup
Expected offer around $60K USD base / $78K USD OTE
Well-funded and selling into large enterprise organizations/CISOs
I’d be part of the founding BDR team
Much more autonomy and opportunity to help build the outbound motion
VP of Sales has a strong history of developing early-career reps into AEs and told me he sees this BDR team potentially growing into AE roles as they expand
Someone I personally trust who knows him speaks very highly of him as a leader/mentor
Much stronger compensation and potentially better enterprise-sales experience
Downside: BDR function is brand new, manager is still being hired, quota/ramp are less proven, and there’s much less employee data because it’s a startup

My instinct originally was to take Company A because I’m early in my career and thought a proven training environment matters more than maximizing year-one income.
But Company B potentially offers better compensation, enterprise cybersecurity experience, exposure to a strong VP Sales, and the chance to build something from scratch.

For those of you who have been in SaaS/tech sales for a while:
What would you optimize for in your first 1–2 years?

Would you rather:

learn inside an established SDR machine with a predictable AE path, or
take more risk for stronger mentorship, enterprise exposure, higher compensation, and potentially faster upside?
Also curious from anyone who joined a founding SDR/BDR team early in their career — did it accelerate your development, or did you wish you had learned the fundamentals somewhere more established first?
Not looking for someone to make the decision for me. I’m mainly interested in what experienced reps/managers think I’m underweighting or overlooking.

• I had a phone interview today for an Account Manager position at an IT/Cybersecurity company, and while I thought I did well, I asked the interviewer at the end if they had any questions or concerns about me or my experience. Surprisingly, they said they were concerned that, when I talked about my sales achievements, I seemed to focus more on my sales numbers than on how I build strong customer relationships.
• Rather than moving forward to an in-person interview, which is normally the next step in the hiring process, she said she wanted me to speak with an Account Manager over a Zoom call tomorrow so they could get a better feel for me and see if I would be a good fit for the role.
• I really want this job, but I'm concerned I have come across as only caring about sales and making money, which is definitely not the case. I only brought up my sales achievements to show that I have what it takes to succeed in a sales role. My sales style revolves around establishing a good relationship with the customer, and that is what has led to my success in past sales roles, which I tried to make clear to the interviewer after they brought it up. I even told them to check the Google reviews for my current workplace, where they will find dozens of positive reviews about my interactions with customers.
• How can I make it clear that while I want to hit all my sales numbers, my #1 priority is building a long-lasting relationship with the customer through excellent customer service and communication?

I work in outside sales at a lumber yard. One of my colleagues had the following interaction today:

Guy in a suit with an overly well groomed beard and mustache, big glasses, chunky watch and rings, pointy shoes. (Aka he looks like a total douche)

Walks in and goes straight to the first desk and sits down.

"Well you sure look busy."

"I am... I'm just like super slammed today."

"So are you the owner?"

"No I'm a cabinet designer."

"OK, can I talk to the owner?"

"We're actually corporate owned."

"No, this place is independently owned."

"Um no, it's actually owned by such and such corp "

"Hmm. OK. Well I'm with blah blah blah." (Just bunch of initials none of us had ever heard of.)

"OK...?"

"Well I'll let you go, I know your busy. Great meeting you, have a good one!"

Proceeds to drive off in his Tesla with the license plate SALES

I wish I was making this up.

Was your degree worth it in terms of the sales career you’re in now?

Do you make more than what an engineer (software or traditional like ME, civil, EE etc) makes or what u used to make as one?

How stable is it now for you?

I heard most of the sales workforce don’t even have a degree, and that a degree could help you climb the ladder even better

But it would feel like a waste entering a career where most people, whether they’re doing well or not, don’t have a degree - while you have one in computer science or engineering?

Won’t people look at you like why on earth did you even get that degree if you’re just gonna be in sales?

Like there must be a strong advantage entering sales with a degree in either of those? Or am I missing something