Using Humor in Sales: Best Practices for Outreach

Introduction

Most B2B buyers’ inboxes look the same: stiff subject lines, buzzword soup, and the occasional all-caps "QUICK QUESTION" that nobody asked for. On the phone side, prospects brace for another robotic script the second they hear, "How are you today?".

Meanwhile, research keeps telling us something obvious: people like to laugh. In Oracle’s global Happiness Report, 91% of people said they prefer brands that are funny, and 77% said they’re more likely to buy from a salesperson who makes them laugh. And yet, most B2B sales teams treat humor like a live grenade.

This guide is about using humor as a tool, not a gimmick. We’ll break down:

• Why humor works in B2B outreach from a psychological and data perspective
• Where to use it in cold emails, calls, and multichannel sequences
• Best practices that keep you on the right side of "clever" vs. "cringe"
• How to train SDRs and operationalize humor safely
• How SalesHive uses AI and SDR teams to make this work at scale

If you’ve ever thought, "Our outreach sounds nothing like how we actually talk to customers," this one’s for you.

Why Humor Works in B2B Sales Outreach

Buyers Are Human First, Job Titles Second

B2B marketing research has historically leaned into rational appeals, business cases, ROI, features. But a growing body of work shows emotional appeals (including humor) materially improve how people respond to messages.

A meta-analysis of 369 correlations on humor in advertising found that humor significantly enhances attention, attitude toward the ad, and positive affect, and even modestly increases purchase intention. More recent reviews show humor-focused content can make ads over 30% more effective and around 37% more memorable than non-humorous versions.

That maps directly onto outbound sales:

• Attention → Opens and callbacks
• Positive affect → Fewer defensive reactions, more openness to a short pitch
• Memorability → You’re the one rep they remember when the problem flares up

Humor as a Pattern Interrupt

Every touch you send is competing with hundreds of other notifications. Humor acts as a "pattern interrupt", it breaks the default mental script of "ignore, delete, decline."

A funny or unexpected line leverages expectancy violation theory: when communication deviates from what someone expects, they pay more attention and reassess the interaction.

In sales terms:

• A normal subject line like `Q3 vendor question` is invisible.
• A playful one like `Spreadsheets called. They want their CRM back` makes the brain do a double-take.

You’ve bought a split second of curiosity. If you use it well, by immediately tying into a relevant pain, you earn a reply or at least a fair hearing.

Humor Lowers Defenses and Builds Warmth

Cold outreach is inherently intrusive. Humor, when used lightly, signals, "I know this is a bit of an interruption; I’m human about it."

Oracle’s research found that 48% of people don’t feel they have a real relationship with a brand unless it makes them smile or laugh, and 41% would walk away from a brand that never does. That’s emotional language, relationship, walk away, about something as "dry" as brand communication.

For sales, those same dynamics extend to people:

• 77% of respondents in the same research said they’re more likely to buy from a funny salesperson.
• That doesn’t mean you need to be a stand-up comic; it means prospects reward reps who make interactions feel lighter and more human.

Buyers Are Starved for Interesting B2B Content

There’s also a big boredom gap you can exploit. One analysis of B2B content and humor notes that around 48% of buyers are bored with contemporary B2B content and want more creative, humorous material from brands.

If you’ve ever slogged through a three-paragraph value proposition full of jargon… you know exactly what they mean.

Put differently: the bar to be "refreshingly human" in B2B is incredibly low.

Where to Use Humor in Outbound Sales (Without Getting Fired)

Humor is not a universal spice. There are safer and riskier places to sprinkle it.

1. Email Outreach

Email is the easiest channel for controlled humor experiments: it’s asynchronous, testable, and scalable.

Subject Lines: Your Safest Playground

Oracle’s global data shows 69% of people would open an email if the subject line were funnier, yet only 24% of business leaders say they actively use humor in email marketing. That gap is where your SDR team can win.

Examples (B2B-appropriate):

• `Is your CRM allergic to adoption?`
• `I broke up with my spreadsheets (it’s not them, it’s you)`
• `Quick question about your Q4 hair-on-fire projects`

All of these:

• Reference a real pain (CRM usage, spreadsheet chaos, Q4 crunch)
• Are safe for almost any industry
• Set up a natural transition into the body copy

Openers: One Line, Then Business

Once they open the email, resist the urge to keep joking. A single line is plenty.

Example structure:

• Line 1 (humor): `Saw you’re hiring three new AEs, guessing your SDRs’ calendars now look like Tetris on hard mode.`
• Line 2-3 (empathy/value): `We help SaaS teams keep those reps at 3-5 qualified demos a week without burning out the SDR team.`
• Rest (proof + CTA): Brief social proof, then a simple ask for a 15-20 minute call.

SalesHive’s internal tests back this up: campaigns with a light humorous hook and strong value prop have driven 18-34% higher open rates, 22% more meetings booked, and roughly 15% faster deal velocity across B2B clients when compared to straight, no-humor variants.

PS Lines: Optional Extra

If you want to get a bit more personality in without cluttering the core message, the PS is your friend.

• `PS, If you’ve already solved SDR burnout, please reply anyway. I have follow-up questions.`

This is low-risk: it doesn’t affect clarity, and it gives personality-loving prospects another reason to respond.

2. Cold Calling

Humor on calls is about tone and pattern interrupt, not set-up/punchline.

The first 5-10 seconds of a cold call decide if you get hung up on. A tiny bit of self-aware humor can buy you permission.

Example openers:

• `Hey Alex, it’s Jordan with Acme. Don’t worry, this is a cold call, you can hang up in 30 seconds if it’s not relevant. Fair?`
• `I know you weren’t sitting there hoping a sales rep would call you… but I think this might actually save your team some time.`

Reps on communities like r/salestechniques share similar pattern-interrupt openers that acknowledge the awkwardness and often get a chuckle before moving into a succinct pitch.

Key rules for calls:

• Keep the humorous part under 5 seconds.
• Never joke about the prospect personally.
• Use the laugh (if you get one) as your segue into a direct "reason for my call" and a crisp value statement.

3. LinkedIn and Social Touches

On LinkedIn, humor is more about overall persona and occasional posts than every DM being a joke.

Best practices:

• Post short, relatable stories about bad processes, tools, or meetings your ICP faces.
• Use witty one-liners in comments on prospects’ posts, but always add real insight.
• In DMs, keep humor extremely light (one line at most), and only after some engagement.

Remember: prospects might screenshot anything you send. Keep it work-safe and brand-safe.

4. Voicemails

Voicemail is where most reps go full monotone. A tiny bit of levity can differentiate you.

Example:

"Hey Priya, it’s Dan with Northstar. Promise this is the only voicemail I’ll leave you this week. The reason I’m calling is we’ve helped other RevOps leaders stop living in spreadsheet hell when it comes to forecasting. If that’s even on your radar, I’ll send a short email now, reply there if you’d like a quick look."

The joke here is subtle, acknowledging voicemail fatigue and "spreadsheet hell", but it makes you sound like a person, not a robocall.

Best Practices: A Framework for Using Humor in Outreach

Let’s get tactical. Here’s a simple framework to keep humor useful and safe.

1. Anchor Humor in Insight, Not Randomness

Research on humor in B2B advertising shows that related humor, jokes that connect to the product or problem, boosts attitudes toward the ad and the brand; unrelated humor often doesn’t.

In outreach, that means:

• Don’t slap a random meme onto an email about security audits.
• Make jokes about the pain your solution addresses (manual work, misaligned teams, tech debt), or the absurdity of the old way.

Bad:

• Meme about a TV show with no tie-in, sent to a CFO who’s never seen it.

Good:

• `Subject: Forecasting using vibes and spreadsheets`
• Body connects to your forecasting platform.

Humor should reinforce the message, not distract from it.

2. Pick Safe Humor Types for B2B

Some humor categories are much safer than others in sales.

Generally safe:

• Self-deprecation (about you as the rep or your job)
• Shared enemy (manual processes, bureaucracy, outdated tools)
• Hyperbole/sarcasm about situations, not people
• Light wordplay and puns on industry terms

Generally risky:

• Anything touching politics, religion, identity, or sensitive social issues
• Jokes about the prospect’s company, product, or personal situation
• Dark humor or "edgy" sarcasm

A simple test: "Would I comfortably say this joke to a new customer in a conference hallway, in front of their boss?" If the answer isn’t a clear yes, don’t put it in a cold email.

3. Keep It Short, One Moment of Levity, Not a Comedy Routine

Meta-analyses of humorous ads show that while humor boosts attention and positive attitudes, overdoing it can actually distract from core messaging and weaken persuasion.

In outbound:

• Limit yourself to one humorous element per touch: subject line or first line or PS, not all three.
• On calls, think one short line, then business.

If a prospect has to wade through three jokes before they understand why you’re emailing, you've overcooked it.

4. Align Humor With Your Brand and ICP

Your tone in outreach can’t be totally divorced from your brand.

• Selling dev tools to startups? You can probably be bolder with memes and slang.
• Selling compliance software to banks? Stick to dry wit and gentle observations.

Also consider seniority:

• Managers and ICs often respond better to more informal, meme-like content.
• C-levels and boards expect brevity and gravitate toward understated humor.

Create a simple grid: vertical × persona × humor intensity (0-3). Use that to design different versions of the same sequence.

5. Use Data, Not Gut Feelings

Marketers have known for years that humor can dramatically increase recall and brand favorability, but it doesn’t automatically drive sales, execution matters.

SalesHive’s A/B tests highlight this nuance:

• Short puns in subject lines → 22% higher opens
• Meme references → 31% higher engagement from tech startups
• GIFs in signatures → 17% lower response rates in professional segments

The takeaway: treat humor like any other variable in your sequence and let the metrics decide.

Operationalizing Humor in Your SDR Team

You don’t need a team of comedians. You need structure.

Step 1: Build a One-Page Humor Playbook

Create a simple internal guide that covers:

1. Why you’re using humor (pattern interrupt, warmth, memorability).
2. Approved humor types with examples: self-deprecation, shared enemy, industry in-jokes.
3. Banned topics: politics, religion, anything that could be construed as discriminatory or mocking prospects.
4. Sample lines that have worked in your tests.
5. Review process for new humorous templates.

Make this part of SDR onboarding. They should know the boundaries on day one.

Step 2: Template With Room for Personality

Give reps scaffolding, not fully rigid scripts:

• A pre-approved subject line bank (some humorous, some neutral)
• Email templates with optional humorous first-line variants
• Call openers with bracketed lines they can tweak to match their voice

Example email scaffold:

• Subject: `[Pain-based pun or straight version]`
• Line 1 (optional humor): `[Approved one-liner about their world]`
• Line 2-4: Problem + what you do
• Line 5-6: Social proof
• CTA: 1 clear ask
• PS (optional humor): `[Optional, safe PS joke]`

Step 3: Train With Real Recordings and Replies

Theory is fine, but nothing teaches like hearing or reading what actually worked.

In weekly sales meetings:

• Listen to 2-3 call clips where humor clearly opened up the prospect, and dissect why.
• Review email threads where a humorous line got a positive response. ("OK, you got my attention with that subject line.")
• Do the same with failures: share a joke that fell flat and discuss how to tighten or remove it.

Over time, you’ll develop an intuition for your audience’s comfort zone.

Step 4: Use AI to Scale Safe Personalization

AI can make humor scalable if you keep humans in the loop.

SalesHive’s eMod engine, for example, automatically researches each prospect (role, company, recent events) and weaves in tailored hooks that often include light, relevant humor, like referencing a recent funding round or a job change with a playful nod, while preserving the core sales message.

Your team can do something similar with AI tools:

1. Feed the AI your ICP, tone guidelines, and example jokes that worked.
2. Have it generate multiple subject lines and openers per segment.
3. Let SDRs select and lightly edit the best ones.
4. A/B test them against your control versions.

AI proposes; humans approve.

Step 5: Instrument Your Data

To know if humor is paying off, you need visibility.

Set up tracking so you can filter performance by "humor-enabled" vs. "neutral" templates:

• Tag templates or sequences that contain humor.
• Track:
• Open rates
• Reply rates (and % positive vs. negative)
• Meetings booked
• Opps created and pipeline value
• Review monthly or quarterly.

If humorous emails show higher opens but lower meeting conversion, your jokes may be attracting curiosity but not the right buyers, or they may be overshadowing your ask.

How This Applies to Your Sales Team

Let’s make this concrete. Here’s a 30-day plan to responsibly test humor in your outbound.

Week 1: Audit and Design

• Audit current outreach: Pull 2-3 of your main sequences and highlight every line that tries to be funny (you may find… none).
• Identify easy wins: Usually subject lines, first lines, and voicemails.
• Draft your Humor Playbook: One page, max. Get leadership sign-off so reps know what’s allowed.

Week 2: Build and Approve Variants

• Have a small squad (1-2 SDRs + manager) draft:
• 10 humorous subject lines per key sequence
• 3-5 optional humorous opening lines per ICP
• 2-3 cold call openers using light self-awareness
• Run these through:
• Legal/compliance if needed
• Brand/marketing for tone alignment
• Peer review with experienced reps

Week 3: Controlled A/B Tests

• Pick one campaign per channel (email + phone) to test.
• For email:
• 50% of prospects get the humorous subject line / opener
• 50% get your current best-performing neutral version
• For phone:
• Reps use the new opener on a defined subset (e.g., all calls to mid-market ops leaders) and tag results.

Track:

• Open and reply rate (email)
• Positive responses and meetings set (both)
• Qualitative feedback ("Loved your subject line" counts)

Week 4: Review and Roll Out (or Roll Back)

• Analyze results: Did humor actually move core KPIs?
• Keep:
• Lines that lift opens and downstream conversions
• Tweak or kill:
• Lines that attract attention but not qualified interest

Update your Humor Playbook with real numbers:

• "This subject line increased open rates from 24% → 31% and booked meetings from 3.1% → 3.8%."

Now you’ve got leadership’s language: humor tied directly to pipeline improvements.

Conclusion + Next Steps

Using humor in sales isn’t about being the funniest rep on LinkedIn. It’s about:

• Breaking through inbox and call fatigue
• Making your team sound like actual humans
• Creating just enough warmth that buyers lower their guard and listen

The data is clear: buyers prefer funny brands, remember funny messages more, and are more likely to buy from funny salespeople. At the same time, most B2B companies are still sending the same dry, mechanical outreach they’ve been sending for a decade.

That gap is your opportunity.

If you want to move fast without reinventing the wheel (or risking your brand), this is exactly where an outsourced SDR partner like SalesHive shines. They’ve already run the experiments across hundreds of clients, baked the results into their AI-powered email engine and cold-calling playbooks, and layered in US-based strategists who know how to keep things professional and on-message.

Whether you build this in-house or lean on a partner, the play is the same:

1. Start small, one humorous subject line, one call opener.
2. Give your reps guardrails and good examples.
3. Let data, not ego, decide what sticks.

Done right, humor won’t just make prospects smile, it’ll make your pipeline a lot healthier too.