How to eff up your sales email automations

Marketing-sales alignment sounds easy, but it’s not.

This is especially true in sales-led orgs.

Every time there’s a shift from automation to live interaction (or vice versa) there’s a big risk that something will go wrong. And the error will be customer- or prospect-facing.

Marketing needs to stay in line with Sales’ approach.

Sales needs to know how the updates they make in the CRM may or may not trigger automations and impact experience.

The really hard part? This “experience improvement” work really can’t be done in departmental silos.

Today, we’re going to look at an unfortunate post-demo experience.

This is an example of “what not to do” rather than “what to do.”

A quick note: I love celebrating awesome work publicly. But when things don’t go right, I assume good intentions until proven otherwise. Naming and shaming is not my style. For this reason, I’m anonymizing the experience you’re going to read about today.

In this issue you'll see:

• A play-by-play of a disjointed pre-sale customer experience

• The big hidden risk in suboptimal marketing-sales alignment

• What you should do now to protect your own marketing-sales environment from potential pitfalls

Let's dig in.

THE BREAKDOWN

Why email automations can’t be “set it and forget it.”

For your consideration, here's the play-by-play of the experience in question:

• Pre-Demo

  • I took a high-value action (clicked on an ebook promoted in an email campaign).

  • Within 15 minutes, I received SDR outreach via email and LinkedIn inviting me to book a demo.

  • I engaged in some back-and-forth with an SDR. The biggie in the conversation was re: pricing—I wanted a ballpark figure, but the SDR said pricing is custom and I’d have to see a demo to get more details… so I booked a demo.

  • The SDR introduced me to a "product specialist."

  • I was sent a calendar invite that showed the SDR and the product specialist were both attending.

• Demo Day

  • The demo happens:

    • The SDR doesn’t join the call and doesn’t mention she’s not joining the call.

    • The “Product Specialist” is actually an Account Executive.

    • The requested details I shared with the AE and SDR before the demo weren’t read and now I’m repeating myself.

    • Part of the demo includes pricing—the pricing isn’t custom like the SDR mentioned. It’s packaged. It’s tiered. And they only have annual terms.

    • We end the demo aligning on the next steps and go our separate ways.

  • Before the end of the day, the Account Executive sends me a solid follow-up email detailing our discussion and next steps.

Worth noting that you might be reading the list above thinking “yeah, that’s kinda business as usual in a sales-led org.” I agree. That’s the problem.

This is undeniably a poor experience, complete with a sloppy handoff, poor communication and straight-up wrong information provided pre-demo.

Why do we continue to settle for these shit experiences?

ALSO, this is a huge opportunity—particularly in crowded markets—for brands to nail this critical handoff (and obliterate the competition).

But I digress. Let’s continue:

One day after the demo, two sales email automations started triggering simultaneously… and the experience went from poor to very bad, very fast:

1. The single-email downgrade sales automation:

   • Automation goal: Recover the sale with a downgrade offer.

   • Subject line: Was price the issue? Check out {COMPANY} again!

   • Sender: VP of Sales Development.

   • Analysis:

     1. The objection is directionally correct but lacks nuance specific to my conversation with the AE. And the nuance matters—terms and price are different objections. As a result, the offer presented and the messaging used to present that offer miss the mark because it doesn’t address the real objection.

     2. This is the hard thing about triggering email automations based on CRM downgrade reasoning: downgrade reasoning is typically selected via a single-select list. The list itself may lack the granularity required to reflect these nuances—that’s not an AE issue, that’s a CRM configuration issue.

     3. The offer presented—in combination with the company’s price-gating practices—made me feel like a sucker. Suddenly, they had a new, drastically less expensive offer available. My perception at this point is that I would’ve been an overpaying sucker if I said “yes” in the demo. By not publicly publishing pricing, this company has intentionally created a buying context that breeds mistrust.

   • Risk: Not-quite-accurate CRM configurations that trigger a poor-fit downgrade automation.

   • Consequence: Low resonance messaging that creates a bizarre buying experience where the buyer feels misunderstood and the offer further erodes trust in the vendor.

2. The multi-email demo invitation automation:

   • Automation goal: Book a demo.

   • Sender: SDR I booked a demo through.

   • Cadence + Subject Lines:

     1. Day 0, Email 1: Subject line: You know us for {KEY FEATURE}, but we’re so much more

     2. +2 Days, Email 2: Subject line: Checking in to answer questions about {COMPANY}

     3. +4 Days, Email 3: Subject line: Still interested?

     4. +2 Days, Email 4: Subject line: Before parting ways

   • Analysis:

     1. At this point I’d already booked AND attended a demo, so this sequence was totally misaligned with my buying journey.

     2. Worth also pointing out that the subject lines alone indicate how product-focused these emails are. There was barely any mention of how the product would enable me to reach my goals. (A classic case of placing the product as the hero instead of the reader.)

   • Risk: Either CRM hygiene (for example, forgetting to mark me as “Attended”) or a poorly configured trigger is the culprit for what I hope is a mistake.

   • Consequence: Misaligned, irrelevant messaging overwhelming my inbox.

This wasn’t a good buying experience. But it wasn’t all bad, either. Here’s what worked (kinda):

• Quick response to high-value actions (ebook download triggered outreach within 15 minutes).

• Solid demo follow-up email detailing discussion points and next steps.

• An attempt to address objections and re-engage prospects.

Here’s what needs fixing:

Problem #1: Conflicting email automations fired consecutively after the demo ended.

Fix #1: Configure triggers and/or your automations to include mechanisms that prevent this from happening. There are several ways to do this—most of them are tedious—but it’ll help prevent this type of situation.

Problem #2: Downgrade email messaging lacks consideration for potential nuances in a pricing objection.

Fix #2: A couple of solutions here:

• They could configure a new downgrade reason to better align with the actual objection. (This is a good option if the downgrade reason I provided is fairly common.)

• They could rethink the offer presented in the downgrade.

Problem #3: SDR was absent from the scheduled demo without acknowledgement or explanation.

Fix #3: If the SDR didn’t plan to attend, don’t set the expectation. If they planned to attend, but couldn’t, have a plan to very simply address this, either via a quick email or by the AE in the call.

Problem #4: AE presented as a “Product Specialist.”

Fix #4: Be honest about who you are and what you do. This is B2B and I’m a B2B freakin’ marketer. You don’t think I know the old “don’t tell them you’re a salesperson” trick? Pretending you’re something you’re not is weird. Stop it.

Problem #5: Discrepancy between "custom" pricing (as stated by SDR) and predefined packages (presented by the AE).

Fix #5: Be freakin’ consistent. Whether this was a real case of the right hand not talking to the left, I don’t know. But this miscommunication—in combination with price-gating—left me feeling like this could’ve been an intentional strategy to get folks on a demo at all costs, which is dumb. Wouldn’t it be better for your team to meet with knowledgeable and qualified prospects? I’d be curious to know how individuals and departments are being goaled behind the scenes, because this smells like poor-fit KPIs.

Problem #6: No public pricing.

Fix #6: When are we going to stop this ridiculous practice? If you work for (or with) an org that still practices price gating, go read Emily Kramer’s post on the topic. Kramer provides plenty of helpful strategies to overcome this antiquated practice.

THE PSYCHOLOGY

Trust is earned, not given.

Let's talk about the elephant in the room: trust. Or in this case, distrust.

Trust isn't just some fluffy concept we throw around in team-building exercises.

In B2B, trust is a big part of what turns "maybe" into "take my money."

Don't believe me? Check this out:

• A recent study (2022) examined commitment and trust in consumers’ purchasing decisions. They determined that both online trust and commitment show positive correlations with an actual purchase.

• A meta-analysis (2024) determined trust is universally important in the current online purchasing environment. This was true whether the respondent was classified as high-income or low-income. And whether the respondent was considered an average internet user or a more sophisticated online shopper.

These are just 2 of many studies published in the last few years on the impact of trust in purchasing decisions. “Trust is important” is not new. Yet so many businesses are still missing the mark.

Intentionally or not, this company is creating a buying experience that breeds distrust.

If you start by playing games and sending mixed signals—even unintentionally—you shouldn’t be surprised when prospects ghost you.

THE ACTIONABLE TIP

You reaaaaally need a customer journey map. (Plus, a bonus tip to help you start small.)

Here's the key strategy you should swipe for creating a cohesive customer experience that drives growth:

Map your entire customer journey, from first contact to raving fan.

Include every email, phone call, text message, LinkedIn message and in-app communication.

Map the technical details—the automation triggers, the exact platform the message is coming from, etc.

Ensure the map is in a central place, where everyone in the org can access it.

By creating a comprehensive map, you ensure everyone understands the impact of each data point and communication on the customer's experience.

If you’re thinking “that sounds like a lot of work,” you’re right. It is. This falls in the "simple but not easy" category.

You may not have the capacity to tackle mapping everything at once.

If that’s you, it’s okay.

Start small.

Work outwards from key touchpoints (like the first demo and the purchase). Make iterative improvements to the customer experience as you work. (This ensures you’ll be rewarded with conversion boosts along the way, which makes doing the work more enjoyable.)

Customer experience is one of those things that’s difficult to get right at scale. But that shouldn’t stop us from trying.