Category Archives: Hiring

Whence Will Come Tomorrow’s Sellers?

Posted on September 3, 2025 | 2 comments

To the extent that most sellers today started their careers as SDRs and to the extent that there is a strong trend to replace SDRs with AI agents (e.g., Piper from Qualified), I have a simple question: whence will come tomorrow’s sellers? [1]

It’s not news that this is a trend across all entry-level work, though I just found a new paper on the topic by three people at Stanford who examined ADP payroll data as the basis for their analysis: Canaries in the Coal Mine? Six Facts about the Recent Employment Effects of Artificial Intelligence. And another one that analyzes resume and job posting data: Generative AI as Seniority-Biased Technological Change: Evidence from U.S. Résumé and Job Posting Data.

But in today’s post, we’re not going to look globally at the topic — no matter how interesting it is — but instead look specifically at just one question: if all the SDRs are AI agents, then where are we going to get sellers from?

I should also explain that I have a dog in the fight. My son Brian just graduated from NYU and started this summer as an SDR at Ramp. (If you’re a US-based company with 150+ employees and interested in spend management, please let me know and I can connect you.) I recommended that he take the job because it’s an amazing company, they have built an excellent sales machine (and the early-career learning on how to do things right is invaluable), and he definitely has both the raw material and the mettle to be successful in technology sales. But as I made the recommendation, I couldn’t help but wonder if he’d be in the final cohort of human SDRs.

My question actually has two parts, so let’s take them one at a time: (i) an assumption that SDRs will be replaced with AI agents, and (ii) the realization that doing so would seriously interrupt the sales career development pipeline.

Will All SDRs Be Agents?

I think the answer here is no, though I do think a good number of them will be. One easy division is inbound vs. outbound. Inbound SDRs primarily qualify and route people with intent (“hand raisers”) to sellers for a discovery and qualification meeting. Input: MQLs. Output: stage-1 opportunities. Outbound SDRs focus on some set of target accounts and work them via outreach sequences in order to get them to take a meeting. Input: contacts. Output: stage-1 opportunities. While they might also receive MQLs from their target accounts, they start higher in the funnel and are more responsible for developing interest in a meeting than someone who downloaded an asset, like it, and wants to speak to a seller.

I believe inbound SDRs provide less value than outbound SDRs and their job is more automatable. Ergo, I think inbound SDRs will be quickly replaced by AI or superannuated by targeted, hybrid inbound/outbound models (i.e., my job is to get into Citibank and I’ll take all the names, leads, and MQLs we have and leverage them to get meetings within the account).

I think outbound SDRs are here to stay. And Ramp, for what it’s worth, seems to agree. I know they’ve onboarded another cohort since Brian’s and they seem to believe that their SDR model works quite well for them. So if the old career path was inbound-SDR into outbound-SDR, I think the new one will start with a hybrid. You’re just an SDR and your job is to get meetings within some target. Sometimes you’ll have a lot of inbound interest to work with, sometimes you won’t.

The first-principles argument here is simple. When automated outreach sequences are table-stakes that every firm can easily do, the only way to break through the AI-generated and AI-automated noise will be via some combination of people/execution, message, and air support [2]. That’s why we’ll still need SDRs — and good ones — in the future.

Where Will We Find Tomorrow’s Sellers?

Since I believe there will be SDRs in the future, I think we’ll find our future sellers there. But in case that’s wrong, let’s examine where we might find them additionally or instead. I’m old enough to remember life before SDRs. So where did we find salesreps back then and where might we find them in the future?

  • Junior sales roles. You’d work your up from smaller companies to bigger ones and from managing smaller accounts to bigger ones. This should still work.
  • Sales training programs. Some companies were famous for their sales training programs, like Xerox or IBM. I’d differentiate those who emphasized entry-level sales training from those who hired sellers with some experience and who emphasized sales onboarding in a particular message or methodology (e.g., Salesforce, PTC). In the future, large companies who find themselves with a talent gap may need to create such programs, substituting Darwinian survival in the SDR ranks for a formal, and presumably demanding, training program. Once established, these companies will be targets for everyone else’s recruiting.
  • Sales consultants. A difficult path but those who survive the transition are often your best sellers. Everytime I hear an SC complain about salesrep compensation, I say the same thing: “quotas are available.” Go grab one and see how you do. (Or don’t and stop complaining,)
  • Customer success. I think this is an under-developed career path and hopefully, as CS gets more business-oriented and account-management-focused, that customer success will be more of a stepping stone into sales. Think: I developed my prospecting muscle as an SDR, I developed my closing and account management muscles as a CSM, and now I’m ready to be a salesrep.

As the SDR ranks shrink due to the pressure brought by AI, companies will have to be more creative about where they find their salespeople. Some will certainly walk up the SDR path. Others, the junior sales path. Some, the top sales training path. But I don’t believe there will be a shortage of sellers in the future. Just a shortage of good ones, as there is today.

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Notes

[1] Turns out that while both “whence” and “from whence” can be considered correct, technically standalone whence is still better in my humble opinion because whence means “from where” so “from whence” is, well, redundant.

[2] In the form of marketing, awareness, reputation, brand, etc.

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Posted in Career, Hiring, Sales, Startups

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These People Aren’t Gods: How European Founders Can Stop Making The #1 Mistake in US Recruiting

Posted on May 18, 2024 | 5 comments

“When you read their profiles and interview them, you think one thing:  these people are gods.”  — European founder on early US hiring.

Despite numerous warnings, I continue to see many European founders fall into the same trap when it comes to hiring in the first years of their US expansion.  Sadly, it feels like one of those lessons you can only learn from experience.  That’s painful because failing on your first US hires comes at a high cost in both dollars and, more importantly, time. 

So, I thought I’d take one more run at solving this problem, based on a chat I had the other day with a European founder.

What causes the “these people are gods” problem? We Americans are:

  • Natural storytellers who build narratives that can potentially mislead.
  • Take credit much more freely than Europeans.
  • Embellish our resumes and profiles, often turning the hype up to 11.

That’s why behavioral interviewing — drilling down into claims, asking “tell me about a time” questions that describe specific moments — is so important in the US. Here’s an example question sequence:

“So, you ran the budget process in 2023 as the head of finance?”

“Tell me how you laid out the process, the milestones, and timing?”

“Did anyone have problems with it?  Were there any disagreements?”

“When you ran the first budget meeting, what major challenge did you encounter and how did you manage it?” 

This approach eliminates generic answers discussing budgeting philosophy, telling you instead how they manage a budget process and, most importantly, whether they actually did.  Because few embellishers can survive multi-layer, drill-down questioning, you might eventually get a response like, “well, the CFO actually laid out the process that year and ran the first meeting.”

In the US we’re used to discounting career claims.  We drill down.  We ask, “what precise role did you play?” We use behavioral questions.  We check references, both those provided and backdoor.  It’s all a normal part of the process.  We do it without thinking.

But European founders are not used to all this.  They come from an understated culture where people tend to discount their accomplishments. To understand a European resume, an American might need to amplify it.  Think:  “yes, we grew the company from $20M to $200M but I was only part of the team that did that,” when they were actually its leader who built it from nothing.

What happens when a culture of understated accomplishment meets a culture of overstated achievement?   

“These people are gods.”  That’s what happens. 

Worse yet, remember this happens in the context of hiring your first US employees, who are typically salespeople and ergo top decile in storytelling and embellishment.

It’s a wonder that anyone successfully expands at all. 

Since this appears to be a lesson best learned by experience, I discovered a great trick the other day chatting with a European founder.  Provided you’ve already begun your US expansion:

Go look at the LinkedIn profiles of the first people you hired and then subsequently fired and see what they say today about their experience at your company.  You might be quite surprised at what you find.

Or, if you’re not that far along, go look at the LinkedIn profiles of the people you’ve hired and who are still on board.  Now that you know them, what do you think of how they described their past experience? How are they describing their current experience?

In both cases, you’ll get real, first-hand experience with American resume and profile inflation that should help you not just intellectually — but viscerally — understand the problem.  And it appears that without this visceral understanding, in many cases you won’t be able to fix it.

The alternative is literally to lose 12-24 months building, firing, and rebuilding your entire US team.  And I’m desperately hoping to help you avoid doing that.

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Do You Want to be Judged on Intentions or Results?

Posted on April 18, 2017 | 5 comments

It was early in my career, maybe 8 years in, and I was director of product marketing at a startup.  One day, my peer, the directof of marketing programs hit me with this in an ops review meeting:

You want to be judged on intentions, not results.

I recall being dumbfounded at the time.  Holy cow, I thought.  Is he right?  Am I standing up arguing about mitigating factors and how things might have been when all the other people in the room were thinking only about black-and-white results?

It was one of those rare phrases that really stuck with me because, among other reasons, he was so right.  I wasn’t debating whether things happened or not.  I wasn’t making excuses or being defensive.  But I was very much judging our performance in the theoretical, hermetically sealed context of what might have been.

Kind of like sales saying a deal slipped instead of did not close.   Or marketing saying we got all the MQLs but didn’t get the requisite pipeline.  Or alliances saying that we signed up the 4 new partners, but didn’t get the new opportunities that were supposed to come with them.

Which phrase of the following sentence matters more — the first part or the second?

We did what we were supposed to, but it didn’t have the desired effect.

We would have gotten the 30 MQLS from the event if it hadn’t snowed in Boston.  But who decided to tempt fate by doing a live event in Boston in February?  People who want to be judged on intentions think about the snowstorm; people who want to be judged on results think about the MQLs.

People who want to judged on intentions build in what they see as “reasons” (which others typically see as “excuses”) for results not being achieved.

I’m six months late hiring the PR manager, but that’s because it’s hard to find great PR people right now.  (And you don’t want me to hire a bad one, do you?)

No, I don’t want you to hire a bad one.  I want you to hire a great one and I wanted you to hire them 6 months ago.  Do you think every other PR manager search in the valley took 6 months more than plan?  I don’t.

Fine lines exist here, no doubt.  Sometimes reasons are reasons and sometimes they are actually excuses.  The question isn’t about any one case.  It’s about, deep down, are you judging yourself by intentions or results?

You’d be surprised how many otherwise very solid people get this one thing wrong — and end up career-limited as a result.

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Posted in Entrepreneurship, Hiring, Leadership, Management, Silicon Valley, Startups

How to Manage Your First Sales VP at a Startup

Posted on October 27, 2016 | 2 comments

One of the hardest hires — and one of the hardest jobs — is to be the first VP of sales at a startup.  Why?

  • There is no history / experience
  • Nobody knows what works and what doesn’t work
  • The company may not have a well defined strategy so it’s hard to make a go-to-market strategy that maps to it
  • Any strategy you choose is somewhat complex because it needs to leave room for experimentation
  • If things don’t work the strong default tendency is to blame the VP of sales and sales execution, and not strategy or product.  (Your second VP of sales gets to blame product or strategy — but never your first.)

It’s a tough job, no doubt.  But it’s also tough for a founder or new CEO to manage the first sales VP.

  • The people who sign up for this high-risk duty are often cocksure and difficult to manage
  • They tend to dismiss questions with experienced-based answers (i.e., well we did thing X at company Y and it worked) that make everything sound easy.
  • They tend to smokescreen issues with such dismissals in order to give themselves maximum flexibility.
  • Most founders know little about sales; they’ve typically never worked in sales and it’s not taught in (business) school.

I think the best thing a founder can do to manage this is to conceptually separate two things:

  • How well the sales VP implements the sales model agreed to with the CEO and the board.
  • Whether that model works.

For example, if your team agrees that it wants to focus on Defense as its beachhead market, but still opportunistically experiment horizontally, then you might agree with the sales VP to build a model that creates a focused team on Department of Defense (DoD) and covers the rest of the country horizontally with a enterprise/corporate split.  More specifically, you might decide to:

  • Create a team of 3 quota carrying reps (QCRs) selling to the DoD who each have 10+ years experience selling to the DoD, ideally holding top secret clearances, supported by 2 sales consultants (SCs) and 2 business development reps (BDRs) with the entire team located in a Regus office in McLean, VA and everyone living with a one-hour commute of that office.
  • Hire 2 enterprise QCRs, one for the East and one for the West, the former in McLean and the latter in SF, each calling only on $1B+ revenue companies, each supported by 1 local SC, and 2 BDRs, where the BDRs are located at corporate (in SF).  Each enterprise QCR must have 10+ years experience selling software in the company’s category.
  • Hire 2 corporate reps in SF, each sharing 1 SC, and supported by 2 BDRs calling on sub $1B revenue companies.  Each corporate rep must have 5+ years experience selling software in the category.

In addition, you would create specific hiring profiles for each role ideally expressed with perhaps 5-10 must-have and 3-5 nice-to-have criteria.

Two key questions:

  • Do we know if this is going to work?  No, of course not.  It’s a startup.  We have no customers, data, or history.  We’ve taken our best guess based on understanding the market and the customers.  But we can’t possibly know if this is going to work.
  • Can we tell if the sales VP is executing it?  Yes.  And you can hold him/her accountable for so doing.  That’s the point.

At far too many startups, the problem is not decomposed in this manner, the specifics are not spelled out, and here’s what happens instead.  The sales VP says:

The plan?  Yes, let me tell you the plan.  I’m going to put boots down in several NFL cities, real sales athletes mind you, the best.  People I’ve worked with who made $500K, $750K, or even $1M in commissions back at Siebel or Salesforce or Oracle.  The best.  We’re going to support those athletes with the best SCs we can find, and we’re going to create an inside sales and SDR team that is bar none, world-class.  We’re going to set standard quotas and ramps and knock this sonofabitch out of the park.  I’ve done this before, I’m matching the patterns, trust me, this is going to be great.

Translation:  we’re going to hire somewhere between 4 and 8 salespeople who I have worked with in the past and who were successful in other companies regardless of whether they have expertise in our space, the skills required in our space, are located where out strategy indicates they should be.  Oh, and since I know a great pharma rep, we’re going to make pharma a territory  and even though he moved to Denver after living in New Jersey, we’ll just fly him out when we need to.  Oh, and the SDRs, I know a great one in Boise and one in Austin.  Yes, and the inside reps, Joe, Joey, Joey-The-Hacksaw was a killer back in the day and even though he’s always on his bass boat and living in Michigan now, we’re going to hire him even though technically speaking our inside reps are supposed to be in SF.

This, as they say in England, is a “dog’s breakfast” of  a sales model.  And when it doesn’t work — and the question is when, not if — what has the company learned?  Precisely and absolutely zero.

If you’re a true optimist, you might say we’ve learned that a bunch of random decisions to hire old cronies scattered across the country with no regard for strategy, models, or hiring profiles, doesn’t work.  But wait a minute — you knew that already; you didn’t need to spend $10M in VC to find out.  (See my post, If We Can’t Have Repeatable Success Can We At Least Have Repeatable Failure?)

By making the model clear — and quite specific as in my example above — you can not only flush out any disagreements in advance, but you can also hold the sales VP accountable for building the model they say they are going to build.  With a squishy model, as my other example shows, you can never actually know because it’s so vague you can’t tell.

This approach actually benefits both sides

  • The CEO benefits because he/she doesn’t get pushed around into agreeing to a vague model that he/she doesn’t understand.  By focusing on specifics the CEO gets to think through the proposed model and decide whether he/she likes it.
  • The Sales VP benefits as well.  While he/she loses some flexibility because hiring can’t be totally opportunistic, on the flip side, if the Sales VP implements the agreed-to model and it doesn’t work, he/she is not totally alone and to blame.  It’s “we failed,” not “you failed.”  Which might lead to a second chance for the sales VP to implement a new model.

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Posted in Hiring, Startups, Strategy, VC

On Hiring: Promote Stars, Not Strangers

Posted on August 25, 2016 | 1 comment

“Well, he’s never been a sales development rep (SDR) manager before, but he has been an SDR for 3 years at another company. The chance to be a manager is why he’d come here.” — Famous Last Words

I can’t tell you the number of times I’ve heard something akin to the above in hiring processes.

Of course he’d come here to get the chance to be a manager.  The question is why his current employer won’t make him one?  They’re the ones who know him.  They’re the ones who’ve worked with him for three years.  What do they know that we don’t?

As a general rule, startups are not the place to learn how to do your job.  At startups, you should hire people who already know how to do the job.  Running the startup, in a high-growth, frenetic environment, is hard enough; you don’t need to be learning how to do your job at the same time.  A key reason startups offer stock options is precisely this:  to incent people who already know how to do the job to do it again by participating in the upside.

This is not to say, reductio ad absurdum, that startups should have no entry-level jobs, never take a bet on inexperienced people, and never promote anyone into management.  That’s a recipe for losing your best people when they decide the company has no interest in their personal development or career path.  The best startup teams are a mix of veterans and up-and-comers, but since — particular for management hires — you need to have a mix, you need to be very careful to whom you give that first-time in-the-job slot.

This is why I made the Star/Stranger Promotion Quadrant.

star promotion

The two axes are simple:  is the person a known star (at this company, i.e., do we all know her and do we all think she’s a star, here) and has the person done the job before (i.e., the actual job, SDR manager in this case, not SDR).

One of the easiest things you can do is to appoint known stars.  This means the person works today at your company in a different role, but wants to do a new job that’s opened up, and has already done that exact job before.  It doesn’t happen that often, but sometimes your director of product management has been director of product marketing before and wants to get back to it.  Awesome.  I call this “appointing” known stars because while the move may involve a titular promotion, in reality it’s more of an appointment than a promotion.  It’s great to let people move around the organization and there should be no shame in ever wanting to move back to something that someone particularly likes doing (or that the company really needs).  I shade this green because it’s low risk.

One of the nicest things you can do is to promote known stars.  For example, take a top-performing SDR who has management potential (an elusive concept, I know, but a whole post unto itself) and give them the chance to run a piece of the SDR team.  I prefer to do this — especially for first-time promotions into management — on a reversible basis.  Since neither side is certain it’s going to work, I believe it’s best to make someone a “team lead” for six months and then assess how it’s going.  If it’s going great, promote them to SDR manager and give them a raise.  If it’s not going well, you haven’t burned the ships on making the person a regular SDR again, working on some skills, and trying again in the future.  I shade this purple because there is some risk involved, but it’s a good risk to take.  People in the organization want see others given the chance to succeed as well as to safely fail in taking on new challenges.

If you lack existing team members with management potential or if your current team has too many first-time (and too few experienced) managers, then your best move is to hire qualified strangers.  While the stranger might want a career step-up, the reality is that most companies hire new people to do jobs they already know how to do.  Cross-company promotions are rare and candidates offered them should be somewhat wary.  Why again are these people willing to make me a CMO for the first time?  Sometimes the reasons are good — e.g., you’ve been a divisional marketing VP at a larger company and move into a startup.  Sometimes the reasons are bad.  Think: why won’t any qualified CMO (who knows this space) take this job?  But, moving back to the employer perspective, I shade this square purple because external hiring is always risky, but you can minimize that risk by hiring people who have done the job before.

This takes us back to the start of this post.  While depending on the kindness of strangers may have worked for Blanche Dubois, as a hiring manager you should not be extending such kindness.  Hiring qualified people is risky enough.  New hires fail all the time — even when they are well qualified for job with lots of relevant prior experience.  Don’t compound the risks of cultural fit, managerial relations, attitude/urgency, and a hundred other soft factors with the risk of not knowing how to do the job in question.  What’s more, do you have time to teach one of your managers to do their job?  Especially when what’s needed is teaching in basic management?  As I often say, VCs are risk isolators more than risk takers, and hiring managers should think the same way.  That’s why you should almost never promote strangers.  (And, as a corollary why strangers should be wary of those willing to promote them.)

That’s why I’ve colored this square red.  Companies should hire outsiders to do jobs that candidates already know how to do.  Promotions are reserved for promising insiders.

Put differently, and from a career planning viewpoint:  “rise up, jump across.”

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Posted in Hiring, Management, Startups