Category Archives: Career

Audio From My Exit Five CMO Leadership Retreat Presentation

Just a quick post to highlight that Exit Five has published the audio from my presentation at their recent leadership retreat.

The presentation was entitled How To Be the CMO Everyone Wants To Work With, and the audio is about an hour long. Exit Five founder Dave Gerhardt published it as Episode 342 of The Dave Gerhardt Show.

Thanks to those who attended and thanks to Dave for inviting me to speak at the event.

Be the CMO Everyone Wants to Work With

I’m a big fan of Dave Gerhardt and the Exit Five marketing community he has built. While I have always liked the idea of peer-networking communities, I think they change from vitamin to painkiller in times of rapid change. Why? Because the playbooks haven’t been written yet.

Take SaaS, for example. Today, you can find scores of blogs — including mine — that talk about how to run SaaS businesses, how to plan SaaS businesses, and how to produce and interpret SaaS metrics. Twenty years ago virtually none of that existed. You needed to figure it out. And one of the best ways to figure it out was to spend time with other people who were doing the same figuring.

There’s a time for timeless wisdom and there’s a time for talking to other people who are doing the same thing as you are, right now. I think AI and the massive disruption it creates in marketing — from content to workflow to performance marketing to analytics — means it’s an awesome time to join a marketing peer-networking community.

I tell this to literally every CMO I work with:

  • Come to me for timeless wisdom (if not fleeting opinions).
  • Join Exit Five (or equivalent) to talk to peers who face the same challenges you do, every day.

That’s not to say that following thought leaders isn’t a great tactic, too. I keep an eye on Emily Kramer, Elena Verna, Carilu Dietrich, Alice de Courcy, and Jon Miller. And I can’t wait for Rand Fishkin’s rumored new book on Zero-Click Marketing. If there are other marketing thought leaders you think I should be following, please let me know.

All this is why I was thrilled when Dave Gerhardt invited me to speak at Exit Five’s Marketing Leadership Retreat on March 19-20 in Phoenix. Given the above, I knew I wasn’t going to be the person delivering fresh-from-the-trenches information on AI tools and methods. The audience is 100x more qualified than I am to do that.

So what did I want to offer up instead? Some timeless wisdom. Specifically, timeless wisdom not just on how to successfully do the CMO job, but on how to be the CMO everyone wants to work with.

Why that topic? And bear in mind it takes a lot for me to pick a title that ends with a preposition. Because I thought it captured the key to success in an important way.

  • It’s not just about doing the job. Yes, that’s quite hard already but if you only focus on that you ironically increase your odds of becoming a statistic.
  • It’s not just about keeping the job. And yes, there’s an art to that, a big part of that is simply remembering to market marketing.
  • It’s about helping the boss do their job which not only increases your strategic value, but makes you more “sticky” in your role.
  • It’s about doing all that while being the CMO that everyone wants to work with (EW2WW)

Why does that last point matter?

  • Marketing is inherently a service organization, so a strong internal customer service orientation never hurts.
  • Being the CMO EW2WW helps you keep your job. With a median tenure of 18-24 months, this should never be too far from a CMO’s mind. Belt and suspenders.
  • If everyone wants to work with you, it helps you find your next job. Board members and recruiters — your top two job sources after peers — will seek you out when the time comes.
  • It might well help you get promoted to COO or CEO. If everyone wants to work with you, they might well give you a shot at the next level.
  • It frames things as a positioning problem. And we know a lot about solving positioning problems, working backwards from a desired result.

Ultimately, I’m saying that CMOs should want to position themselves as the CMO EW2WW.

Put differently: “Marketer, position thyself.

(Adapted without permission from Luke 4:23.)

With that as background, here are the slides from the presentation, embedded below, and downloadable here. I had a fairly miserable time in Gamma building them so apologies for the upside-down funnel, some of the formatting, graphics, and mechanics (e.g., the absence of copyright notice and slide numbers). There is only so much time I’m willing to spend explaining to a chatbot what expression to put on the reflected image of a face in a mirror. And once you drop into PowerPoint to make changes, there seems to be no going back.

Thanks again to Dave for having me and to Allison Saxon for working with me to make it happen.

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.