Category Archives: Career

The Ten Most-Read Kellblog Posts in 2025

I did this analysis last year and it became a popular post, so I figured I’d do the same retrospective today. Following are the ten most-read Kellblog posts in 2025, regardless of the year in which they were written — and it includes some golden oldies.

  1. What it really means to be a manager, director, VP (2015). Now at ten years old, this post is a perennial favorite. I wrote it because I got tired of answering the question and something about my answer clearly struck a note with a lot of people. (Hint: the answer’s not in your job leveling system.)
  2. How to navigate the pipeline crisis (2025). In this post I wrote about what I saw as a general pipeline crisis in the industry, shared some interesting posts on it, and then tried to put myself back in the CMO chair and answer: what would I do about it?
  3. The one key to dealing with senior executives: answer the question! (2012). If the manager vs. director post (above) gets the most traffic, this post gets the most in-person mentions. Think: “Dave, I forwarded your ATFQ post about a dozen times this year.” This issue bothered me 13 years ago when I wrote the post and evidently non-answered questions are still bothering people today. If someone, particularly a customer or an executive, asks you a question: answer it.
  4. Kellblog predictions for 2025 (2025). I scored these an 8 out of 10. Go here to read my predictions for 2026, the 12th annual post in this series. These posts are more industry commentary and analysis than simply a list of things I think are going to happen. And they require Herculean effort. This year’s post was 7,644 words with 166 links and took 65 hours to write.
  5. Your ICP starts as an aspiration and ends as a regression (2025). I love the pithy title of this one. This post discusses the evolution of your ideal customer profile (ICP) which starts out as a wink in the founder’s eye and should, over time, end up the result of a regression analysis. That is, you start out by deciding who you want to focus on and then, over time and as a function of your definition of “success,” the data should tell you.
  6. De-mystifying the growth-adjusted enterprise value to revenue multiple: introducing the ERG ratio (2024). I first heard of the PEG ratio in Peter Lynch’s classic, One Up on Wall Street. This post takes the same idea — growth adjusting — and applies it to price/sales as opposed to price/earnings. Much as I love the metric, I was frankly surprised to see this one up here.
  7. The SaaS Rule of 40 (2017). Another classic, from eight years back. See this year’s predictions to understand why I believe the Rule of 40 might well become the Rule of 60 in 2026.
  8. A CEO’s high-level guide to GTM troubleshooting (2025). An integration and repackaging of a lot of my advice specifically written for the CEO and to help them troubleshoot their go-to-market (GTM) issues. I was happy to see this one up here.
  9. The pipeline progression chart: why I like it better than tracking rolling-four-quarter pipeline (2022). Give the CRO rolling-four-quarter sales targets and I’ll be in favor of tracking rolling-four-quarter pipeline. Meantime, we need to track it by quarter and this chart shows you how. Don’t even get me started on people who want to track annual pipeline.
  10. Six tips on presenting to the board of directors (2025). A post I wrote to help executive staff make a good impression on the board by losing any prior board PTSD, making a deck from scratch (not recycling slides), cutting to the chase, taking certain things offline, and of course ATFQ.

Technically, my Best of Kellogg post also made the list, so if you’ve not checked that out lately, perhaps you should. I’ve recently revised it as I do about once a year.

I was happy to see that five of the ten top posts were from 2025, which I think hits the right balance of healthy re-use of the classics along with some endorsement of my new material. Thanks for reading.

Whence Will Come Tomorrow’s Sellers?

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.

# # #

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.

Six Tips on Presenting to the Board of Directors

So, you’re on the executive staff of a startup and you’ve been asked to present at an upcoming board meeting.  That’s great news. Board exposure is a key benefit of working on the e-staff. You’re getting the chance to build relationships with the venture capitalists and independent directors who sit on your board. These people can help you in many ways, e.g., providing tactical advice, acting more generally as mentors, helping you extend your network, approving your future promotion to a more important position, presenting you with outside board or advisory opportunities, and — when the time comes for it — helping you find your next company.

The board can be a tailwind accelerating your career or a headwind slowing it down. Let’s talk today about how to make a good impression in board meetings and how to start building good relationships with the members of your board.

Here are six tips:

  1. Lose the baggage. If you have authority issues or PTSD from prior board experiences, you need to lose the baggage. That may not be easy — and you may need a therapist to do it — but boards can easily sense passive aggression and inauthentic interactions. I worked with one CRO who viewed board meetings as a necessary evil, something to survive so we can all get back to work. If you feel this way, the odds are the board can tell. (Our board certainly could, and it limited his tenure as a result.)
  2. Make your presentation from scratch. Bad board sessions start with bad slides. Usually, they’re too long and detailed. This typically positions the exec as either “in the weeds” (ergo too junior and in need of an upgrade) or “stonewalling” (i.e., deliberately making an overwhelming deck to stifle conversation). The path to hell begins in the slide sorter, so do not start there. Start with a blank outline to avoid the number one mistake — starting with what you have instead of what the audience needs. Doing so is a false economy and, for chrissake, it’s your board: if anyone deserves a custom presentation, it’s them. So make a custom slides, from scratch.
  3. Cut to the chase. Boards are notoriously impatient. Individual sessions are usually pretty short. There’s no time to warm up with “How ’bout those Yankees?” or several introductory slides, including the tired highlights / lowlights slide. (That slide is appropriate once in a board deck, in the CEO’s update, and if there’s something particularly good or bad in a functional area, it should have already been raised there.) If we’ve had insufficient pipeline for the past two quarters, go immediately to the reasons why and the remediation plan. If you’re not sure what the hot issues are — itself a yellow flag — ask the CEO. Nothing will infuriate a board more than endless warm-up slides that don’t cover the important issues. Beware saying: “Great question, but we’ll get to that on slide 27.” With some boards, you may not still be employed by slide 27.
  4. Make slides that facilitate discussion. Board members like to talk, so let them. Build slides that facilitate a discussion. That usually means first baselining the board with key facts and metrics. (Remember, they might sit on 5 to 10 other boards, so they’re not going to remember everything you talked about last meeting.) Then tee-up a discussion using techniques such as: (i) making a proposal and asking for feedback, (ii) outlining three options (if you really can’t decide) and requesting input on them, or (iii) asking three questions that will help you make the decision. Be authentic. Don’t propose three options if two are patently absurd. This wastes the board’s time and they’ll see through it.
  5. ATFQ (answer the effing question). If, at any time during the meeting, the board asks you a question: answer it. Read this — among the top five Kellblog posts of all time — for advice on how to do so. If asked for your opinion, offer it. Don’t stare at the CEO and then toe the company line. The board is fully aware of the disagree-and-commit principle. They assume you’re committed. They’re asking if you agree.
  6. Ask for relevant follow-up meetings. If you’re the CRO and one of your directors is a former-CRO, ask them for an offline meeting to discuss a hot sales-related topic. While you should spend most of that meeting discussing the advertised topic, you should take a bit of time to get to know each other and start building a relationship. Invite them to a coffee if you can, as opposed to a Zoom. Drive to their office if they invite you.

If you follow this advice, you’ll make a better impression on your board than most and you’ll start to leverage board meetings to set up offline conversations that will hopefully lead to a few career-long and career-changing relationships.

As CJ Gustafson replied when we discussed the idea of building relationships, “oh, you could find a relationship like Scorsese and DiCaprio.” Yes, exactly. That worked out pretty well for both of them.

The Ten Most Read Kellblog Posts in 2024

It’s always fun to go back and look at my stats, and my best-of page (which amazingly came in at #11) is getting sufficiently long that I need to find additional summarization mechanisms.

So this year, I thought I’d share the top-ten Kellblog posts of 2024 (year to date) regardless of the year in which they were written.

  1. Kellblog predictions for 2024. My tenth annual predictions post topped the list. I’m already working on my 2025 predictions which I hope to publish before the end of December.
  2. What it really means to be a manager, director, or VP. Written in 2015, this continues to be a top post every year and, as a result, is the all-time #1 Kellblog post.
  3. The top 7 marketing metrics for a QBR or board meeting. A 2023 post I wrote after a friend asked: “blank slate, what 5 metrics would you present to the board?” I cheated and did 7.
  4. The key to dealing with senior executives: answer the question. Another perennial favorite, this 2012 post is the one people mention to me the most. Think: “I forwarded that to my team!”
  5. The one question to ask before blowing up your customer success team. The first 2024 post on the list, I wrote this to encourage people to take a minute before Slootmanizing their CS department.
  6. Demystifying the growth-adjusted enterprise value to revenue multiple. This 2024 post explains the metric and, in a quest for syllabic parsimony, suggests naming it the ERG ratio, after the PEG ratio.
  7. Go-to-market troubleshooting, let’s take it from the top. If you’re chronically missing new bookings plan, then read this 2024 post and listen to the SaaS Talk episode that covers it.
  8. Target pipeline coverage is not the inverse of win rate. I saw one too many people invert their win rate to set pipeline coverage targets and wrote this 2024 post to show them the error of their ways.
  9. Simplifiers go far, complexifiers get stuck. This classic from 2015 starts with a poignant joke. Question: What does a complexifier call a simplifier? Answer: Boss. Learn why by reading it.
  10. Playing to win vs. playing to make plan: the two very different worlds of Silicon Valley. This 2024 post explores how the valley has fractured into somewhat distinct VC- and PE-backed worlds.

Keep an eye out for my 2025 predictions later this month. And thanks for reading.

Hump? What Hump? Why You Should Listen When Someone Says You’re Doing It Wrong.

Lack of savoir faire, like hypertension, is a silent killer.

There are few symptoms, other than the odd cringe that often goes unnoticed. But the outcomes are clear if the reasons are not:  you’re omitted from meetings, passed over for promotions, underperform in nine-box reviews, find advisors suddenly too busy to work with your company [1], and VCs surprisingly passing on your financing round [2].

The problem is that nobody wants to tell you what’s wrong. It’s like this scene from Young Frankenstein.

Frankenstein: You know, I don’t mean to embarrass you, but I’m a rather brilliant surgeon. Perhaps I could help you with that hump?

Igor: What hump?


It’s just easier to move on.

But make no mistake, these problems can kill your career.  Or, more commonly, simply stall it out. Nothing is more lethal to a career than these eight words: “Kelly’s a great director, but not VP material.” [3]

Savoir faire is related to savvy in English, but not quite the same. I think of savoir faire as know-what as opposed to know-how [4]. Diplomats have great know-what when it comes to knowing what to say or do in a delicate situation. Vintners have great know-how on the subject of making wine.

Savoir faire is thus a social skill and largely about adherence to unwritten rules of conduct. In Silicon Valley, land of engineers, we don’t talk much about social skills [5]. We prefer our numbers, facts, and figures.

But to say these rules are unwritten is not to say they don’t exist [6]. I’ve been repeatedly reminded of them in the past few months, courtesy of several encounters with people who were simply, for lack of a better term, doing it wrong.

More interestingly, when I tried to give these people feedback, the reactions I got were defensive and sometimes hostile. You can argue this is about me, my direct style, or my not having earned the right to offer such feedback. But I believe it was primarily about the nature of the feedback itself.

While giving feedback is always tricky — see Jason Lemkin’s recent announcement that he’s going to stop giving feedback in 2024 — feedback about savoir faire is different:

  • It’s personal, about behavior, and thus even more likely to cause offense
  • It’s seemingly subjective or arbitrary, particularly when you don’t know the rules
  • It’s not up for debate. We’re not debating strategy A vs. B. I’m telling you that you don’t treat a successful founder who just sold his company for $600M like a used-car salesperson.

And this is why most people don’t offer it. There’s almost nothing but downside. It’s easier to simply:

  • Not invite the guest who talked politics to the next dinner party
  • Not return the recruiter’s call seeking a blind reference on the executive who wrote an inappropriate social media farewell thread
  • Become too busy to advise the executive who bungled the introduction to a high-value contact
  • Ghost the founder who wants copious free advice, but who just can’t get around to signing an advisor agreement
  • Say “I need to go mingle” to the clueless employee who challenged you on the utility of MBAs at the company reception [7]

It’s simply not worth the time or risk to explain to these people how dumb they look. And they probably won’t listen anyway. So on they go, like Igor with his hump, unaware of the problem, yet inexplicably not getting results that they want.

If I were to make a tagline for this problem it’d be this:

Savoir Faire: If You Don’t Have It, You Don’t Know.

Almost definitionally [8].

So, this is why, if you ever find yourself lucky enough to be on the receiving end of “you’re doing it wrong” feedback, you should do the following:

  • Realize that you’re receiving it. Think: “Hey, we’re not debating options here. I’m being told I mishandled a situation.”
  • Understand that you’re being offered a gift. The giver certainly knows it’s potentially offensive, but is offering it nevertheless.
  • Recognize that this is likely your last interaction with the giver if you don’t handle the situation well.
  • Avoid defensiveness or debate. They’re telling you the equivalent of “use the silverware from the outside in” or “don’t wear white pants after Labor Day.” They’re not looking for a debate.
  • Avoid rationalizations like “oh, they’re old and that’s how it used to be done.” A lot of things change in Silicon Valley over time. But a lot don’t.
  • Consider the possibility that they may be right. You obviously disagree because they wouldn’t be offering the feedback if you didn’t. The odds of them being correct increase with the size of the experience gap between you.
  • Thank them for offering the feedback. Remember that most people wouldn’t, their intent is likely good, and they probably wouldn’t bother if they didn’t see something they liked.
  • Apologize if you feel it’s indicated. I literally once told a founder, “you mishandled that introduction so badly that it embarrassed me,” and was told in response, “there’s no reason it should have embarrassed you” [9]. This three-fer wiped out working with me, my friend, and quite probably the VC firm that referred him to me. All because they refused to hear what I was saying (“you embarrassed me”) and offer a simple apology in return.

I hope this post helps you develop your career by explaining why, when someone tells you that you’re doing it wrong, that you should perk up and listen.

# # #

Notes

[1] Despite oddly having time for an exploratory meeting.

[2] Despite saying, “we love what you folks are doing and stay in touch.”

[3] Often, in my experience, such damning statements go unchallenged in a group setting, particularly when made by the boss.  The typical response is nods, “oh yes,” “it’s a shame,” and “the world needs directors, too.”

[4] This is an imperfect simplification.  I remember it by defining know-how as about tying a bowline or making beef bourguignonne – i.e., knowing how to do something – technical knowledge.  Know-what is knowing what to say or what to do, particularly in a difficult situation – social knowledge.  Unfortunately, you could just as easily define the latter as know-how:  knowing how to behave at a funeral or knowing how to handle a drunk relative at a party. 

[5] And when we do it’s about arguably naïve ideas like radical transparency. While I like it as a correction to our default behavior, taken literally, it breaks down quickly:  are you going to be radically transparent about the CRO who steps down to enter a rehab program or the planned acquisition that falls through?  In the latter case, such transparency is not only ill-advised, it’s typically a breach of contract (e.g., an NDA).

[6] This begs a question about privilege. You could (correctly) argue that a wealthy upbringing teaches you proper table etiquette at a country club and thus that people who grew up in the bottom wealth quartile would not typically have access to that knowledge.  (See the infamous SAT oarsmen-to-regatta analogy question.)  But I am not talking about either standardized tests or immutable traits, I’m talking about behaviors that can be learned.  While privilege might afford you the advantage of already knowing some of these things, it might not. And the good news is that, either way, they can be learned if you are willing to admit there might be things you don’t know, and if you are lucky enough to encounter someone willing to teach you. 

[7] In this case, the perpetrator was the 28-year-old me squandering a once-in-a-lifetime chat with Bob Waterman, co-author of In Search of Excellence (and a Stanford MBA), by asking a stupid question. You see, there’s a reason why I’m passionate about this topic. I needed a lot of help myself and was usually — but not always — lucky enough to get it.

[8] A derivative of a tagline we once used at Business Objects — Business Intelligence: If You Have It, You Know.

[9] I’m the one who decides if I’m embarrassed, not you.  Whether you would have been, or whether you think I should have been, is beside the point.