Key Takeaways
- Humor is not just for B2C, B2B buyers are humans too. Studies show humorous ads drive a 28% increase in brand connection among B2B buyers and a 20% lift in brand affinity, making prospects more likely to remember and engage with you.
- The safest, highest-ROI way to use humor in sales outreach is through light, relevant pattern interrupts in subject lines, openers, and PS lines, never at the prospect's expense and always tied to a real business problem.
- In one global survey, 69% of people said they would open brand emails more often if the subject lines were funnier, yet only 24% of business leaders actually use humor in email marketing, leaving a huge competitive gap to exploit.
- B2B decision-makers respond to creative messaging: nearly half say they are more likely to look into a product when the advertising uses creativity such as humor or storytelling, and 4 in 10 would recommend those brands to others.
- When implemented well, humorous outreach can move hard numbers: SalesHive has seen campaigns where humor increased email open rates by 18-34%, boosted meeting booking rates by 22%, and improved deal velocity by 15%.
- Humor amplifies what already works, it does not fix bad targeting. Teams that pair humorous copy with tight ICP lists and deep personalization routinely hit reply rates far above the 1-8.5% range most cold email campaigns see.
- You do not need to turn your SDRs into stand-up comedians. A simple framework, relevance, respect, and restraint, plus structured A/B testing is enough to safely roll humor into your cadences starting this week.
B2B buyers are drowning in serious, look-alike outreach, and that makes well-placed humor a real competitive advantage. Research shows 69% of people would open more brand emails if the subject lines were funnier, yet only a minority of companies use humor today. This guide breaks down why humor works in B2B sales outreach, specific techniques for email, calling, and LinkedIn, and how to roll it out across your SDR team without crossing any lines.
Introduction
Let’s be honest: most B2B sales outreach reads like it was written by a committee that hasn’t laughed since the last all-hands. Your prospects’ inboxes are full of subject lines like "Driving synergies across your digital transformation" and cold calls that start with, "Do you have 27 seconds for me to pitch you?" No wonder reply rates are anemic.
Meanwhile, the data is screaming something different: people actually want brands to be funny. A global study from Oracle found that 91% of people prefer brands to be funny, 90% are more likely to remember funny ads, and 69% say they would open brand emails more often if the subject lines were funnier, yet only 24% of business leaders use humor in email marketing at all. MarketingDive
So why is B2B outreach still so buttoned up? Mostly fear. Fear of offending, fear of looking unprofessional, fear of trying something new when quota is on the line.
This guide is about using humor in a way that reduces risk and increases pipeline. We’ll cover:
- Why humor works in B2B (with real stats, not just vibes)
- Principles for using humor without crossing any lines
- Specific techniques for cold email, calling, and LinkedIn
- A testing framework you can roll out with your SDR team
- How SalesHive uses AI-powered personalization plus humor to book more meetings
If you’re looking for a definitive playbook to make your outreach more human, and more effective, without turning your SDRs into stand-up comics, you’re in the right place.
Why Humor Works in B2B Sales Outreach
Buyers are humans first, job titles second
There’s a stubborn myth in B2B that business buyers are cold, hyper-rational robots who only respond to ROI calculators and Gartner quadrants. But the research says otherwise.
A recent study of B2B buyers found that when they see a funny ad, they report a 28% increase in brand connection and a 20% increase in brand affinity, making them more likely to remember and engage with the brand. ScienceDirect At least 70% of B2B buyers in that same research agreed that humor in advertising is effective.
Another LinkedIn analysis of B2B creative showed that humor can drive 65% higher engagement and 42% more form fills compared with more serious creative.
In parallel, Statista reported that nearly half of business decision makers on LinkedIn are more likely to look into a product or service from a company that uses creativity, like humor or storytelling, in its advertising, and 4 in 10 would recommend those products and services to others. Statista
In other words: your buyers do not leave their sense of humor at the firewall. They just rarely see anything worth laughing at in their inbox.
Humor cuts through noise, especially in email
In a world where 43% of people open an email primarily based on the subject line, any edge you can get there matters. HubSpot Humor is one of the most reliable pattern interrupts you can use.
The Oracle “Happiness Report” found that while global email open rates hover around 21%, 69% of people say they would open branded emails more often if the subject lines were funnier. MarketingDive Other marketers have seen up to a 30% increase in email engagement when they A/B test humorous subject lines against straight ones. Saletancy
On the outbound side, most cold email campaigns still sit in the 1-8.5% reply rate range, while highly targeted and personalized campaigns can hit 40-50% response rates. Mailforge Humor layered on top of that personalization acts as a force multiplier: SalesHive’s internal data shows humorous B2B email outreach can increase open rates by 18-34%, boost meeting booking rates by 22%, and improve deal velocity by 15% when executed well.
Emotion speeds up trust and recall
From a brain science perspective, humor is basically emotional superglue:
- It triggers a small hit of dopamine, which improves memory and learning.
- It lowers social defenses, making the other person more open to new information.
- It signals that you understand the shared context, you “get” their world.
That last point is especially important in B2B sales development. Humor says: “I know your pain well enough to make fun of it, not you.” When your outreach makes a prospect feel seen instead of pitched, you’ve already won half the battle.
Principles: Using Humor Without Getting Yourself Fired
Before we get into tactics, we need a few non-negotiable rules. Humor in sales outreach works only when it is:
- Relevant to the buyer’s world
- Respectful of the person and their context
- Restrained enough to support the message, not overshadow it
Think of this as the 3R Framework.
1. Relevance: Joke about the pain, not random stuff
Good sales humor feels like an inside joke between peers. It references:
- Common frustrations (manual reporting, 47-tab spreadsheets, security reviews)
- Organizational realities (three approvals for a Zoom license, anyone?)
- Industry quirks (marketing loving new tools, IT hating new tools)
Bad humor is anything you could copy-paste into a meme page and it would make just as much sense. If the punchline does not require knowledge of the buyer’s world, it does not belong in your outreach.
Litmus test: If you showed the joke to someone outside the industry and they laughed harder than your ICP, it probably is not specific enough.
2. Respect: Punch up or sideways, never down
There are only three safe targets for your jokes:
- Shared enemies: broken processes, outdated tools, compliance overkill
- Your own role: "Yet another SDR in your inbox, I know…"
- Your own solution category: light self-deprecation about vendors that overpromise
You never punch at:
- The prospect’s intelligence, decisions, or company
- Sensitive topics (health, layoffs, politics, identity)
- Real crises or tragedies
You want the prospect laughing with you about the situation, not at anyone.
3. Restraint: Seasoning, not the main course
Humor should be a highlight, not the whole show. A couple of guidelines:
- One humorous element per email (subject line, opener, or PS)
- One quick pattern interrupt in a cold call, then straight to value
- One light touch in a LinkedIn DM or comment
If your prospects remember the joke but forget what you do, you overdid it.
Guardrails for your team
Before you unleash your SDRs, put some basic guardrails in place:
- A one-page humor policy with do’s and don’ts
- Concrete examples of approved subject lines and openers
- Clear rules about legal/compliance review for regulated industries
This is not about killing creativity; it is about making creativity safe to scale.
Techniques: Where and How to Use Humor in Outreach
Let’s talk tactics. Here are the highest-ROI ways to weave humor into cold email, calling, and LinkedIn.
1) Subject lines that earn the open
Your subject line has one job: get the right people to open. Humor is a powerful way to do that without resorting to clickbait.
Types of humorous subject lines
- Shared pain subject lines
- "Your Q4 forecast called. It needs therapy."
- "Manual reporting again? I’m sorry for your loss."
- Playful curiosity
- "I blame your SaaS stack for this email"
- "Tried this trick on another VP… it worked too well"
- Self-deprecating sales humor
- "Yes, it’s a sales email. No, I won’t waste your time"
- "Cold email from a real human (endangered species)"
- Light wordplay (industry-specific puns)
- For data teams: "Our dashboards don’t ghost you (unlike your data)"
- For RevOps: "Removing ‘spreadsheet gymnastics’ from your job description"
Best practices for subject lines
- Keep them around 40-60 characters where possible, that range often performs well for opens and clicks. HubSpot
- Make sure the joke does not obscure the topic. The reader should still know this is about forecasting, reporting, compliance, etc.
- A/B test against a serious control line on the same segment instead of guessing.
2) Email openers that sound like a human
Once the prospect opens, your first 1-2 sentences determine whether they read or bounce.
Examples of effective humorous openers
- Self-aware sales opener:
- Shared pain opener:
- Contextual humor using research:
A small touch of humor here tells the reader, "This is not another robotic sequence," and earns you the 10 extra seconds you need to make your point.
3) PS lines that leave a positive impression
If you’re nervous about putting humor front and center, the PS is a great sandbox.
Examples:
- "PS: If now’s a terrible time, reply with ‘busy’ and I’ll disappear like a bad forecast."
- "PS: If you’re not the right person, feel free to forward this to whoever complains the loudest about [problem]."
- "PS: Promise I won’t send you a calendar link unless you ask. I’m not that kind of salesperson."
These give you personality without risking confusion in the main body.
4) Cold call openers that disarm instead of annoy
On the phone, your tone does most of the work, but a well-placed line can change the energy immediately.
Pattern-interrupt openers
- "Hey Alex, it’s Jamie. Did I catch you in the middle of something terrible, or just mildly inconvenient?"
- "Quick one, I’m a real human, not a robo-dialer, I swear. Do you have 30 seconds for why I called?"
Most prospects have been trained to brace for a pushy pitch. A small joke signals that you are not reading from the same script as everyone else.
Guardrails for phone humor
- Use humor only in the first 10-15 seconds, then pivot to value.
- If the prospect does not laugh or engage, drop it. Do not repeat the joke.
- Never mock their current tools or decisions; frame them as doing the best they can with clunky systems.
5) LinkedIn humor: comments > DMs > posts
LinkedIn has quietly become more comedic. Between 2019 and 2022, the platform saw a 160% increase in members requesting more ways to express humor and a surge in posts using laughter-related emojis, leading LinkedIn to add a “laugh” reaction. Financial Times
For SDRs, this creates three opportunities:
- Comments on prospect posts, light, insightful comments with a touch of humor often outperform generic "Great post" replies and start actual conversations.
- DM follow-ups, after a call or email, a quick message referencing a shared joke from the call can keep the relationship warm.
- Team or company posts, sharing memes or humorous takes on industry challenges can attract your ICP into your orbit before you ever reach out.
Example comment:
"As a recovering spreadsheet addict, that slide about manual forecasting hit a little too hard. Curious how your team is handling it today?"
You’re not trying to be the next LinkedIn comedian, you’re just making your brand feel less like a logo and more like a person.
A Practical Playbook: Rolling Out Humor Across Your Cadences
You do not need to overhaul every touch. Start small, test ruthlessly, then scale what works.
Step 1: Define your humor boundaries
Grab your management, marketing, and (if relevant) legal partners and answer a few questions:
- On a 1-10 scale from "dead serious" to "TikTok brand," where do we want to land?
- Which topics are absolutely off-limits?
- Which personas and industries can handle more playful tone, and which need it subtle?
Turn this into a one-page "Humor Guardrails" doc and make it part of SDR onboarding.
Step 2: Identify 1-2 sequences to pilot
Pick existing cadences that already perform decently and where your ICP skews open-minded:
- Example: outbound to VP Marketing / Demand Gen at mid-market SaaS
- Or: RevOps leaders at high-growth tech companies
Do not start with your most conservative segment (e.g., enterprise banking compliance) on day one.
Step 3: Create A/B test variants
For each chosen sequence, create a simple A/B setup:
- Variant A (Control): Your current best-performing version
- Variant B (Humorous): Same structure and value prop, but:
- Subject line includes a relevant, light joke
- Opener contains one line of shared-pain humor
- Optional PS with another small touch
Example for a RevOps outreach:
- Subject A: "Idea to cut your manual pipeline reporting"
- Subject B: "Your pipeline spreadsheet deserves retirement benefits"
- Opener A: "I saw you oversee revenue operations at Acme and wanted to share a quick idea to reduce manual reporting."
- Opener B: "My guess is that as Head of RevOps at Acme, you’re on a first-name basis with at least one nightmare spreadsheet. Quick idea to retire it gracefully."
Step 4: Run the test on a tight, clean list
Send each version to a small but clearly ICP-aligned segment (50-100 contacts per version to start). Make sure:
- Your domains are warmed and deliverability is healthy
- Your data is accurate (no sense testing humor on bounced emails)
- You are not overlapping contacts between variants
This is where a partner like SalesHive is helpful, our list building and deliverability controls mean you’re testing the copy, not whether your emails land in spam.
Step 5: Measure more than opens
Because humor often lifts opens, you want to look deeper:
- Open rate, Did the subject line do its job?
- Reply rate, Did the humor help or hurt responses?
- Positive reply rate, Did it attract more qualified interest?
- Meetings booked, Did that interest translate into calls?
Keep the humorous elements that lift opens without tanking replies or meetings. Kill anything that gets opens but lower-quality engagement.
Step 6: Build a reusable "humor snippets" library
Once you have winners, do not bury them in one rep’s inbox.
- Add them to your sales playbook or enablement wiki.
- Tag them by persona, industry, and stage.
- Coach SDRs on when and how to use each snippet.
Over time, you end up with a menu of proven lines your whole team can grab from instead of reinventing the wheel.
Concrete Examples You Can Steal (and Tweak)
To make this less theoretical, here are some plug-and-play examples you can adapt.
Example 1: First-touch email to a VP Marketing
Subject: "Your MQL spreadsheet deserves a vacation"
Hi Sarah,
Saw you’re leading demand gen at Apex, which I’m guessing means juggling attribution debates, budget cuts, and at least one MQL spreadsheet that refuses to die.
We help B2B marketing teams consolidate their funnel data so they can:
- See where pipeline is really coming from (without 47 tabs)
- Kill underperforming channels faster
- Give sales a forecast that doesn’t change every Monday
We recently helped a SaaS company in your stage increase SQLs by 27% in 90 days by connecting their paid, content, and outbound data into one view.
Worth a quick 15-minute call to see if any of that maps to what you’re trying to fix this quarter?
Best,
Jake
PS: If you’ve already solved this and your reports are always on time and accurate, I’ll buy you a coffee just to learn your ways.
Example 2: Second-touch "bump" email with humor
Subject: "Re: your overworked dashboards"
Hi Sarah,
Bumping this once in case it got buried under board decks and "quick questions" from sales.
If now’s not the right time to talk dashboards, no worries, just reply with "later" and I’ll check back when your calendar looks less like a game of Tetris.
Otherwise, open to a 15-minute chat next week?
Best,
Jake
Example 3: Cold call opener for a VP Sales
"Hey Mike, this is Laura with Nimbus. Did I catch you in the middle of something terrible, or just mildly inconvenient?
[Prospect chuckles: "Always something."]
Totally get it, I’ll be quick. I’m calling because we’ve been helping VPs of Sales in SaaS get their reps out of CRM data entry hell and back on the phones. Does that sound at all relevant right now, or not really your world?"
Notice: the humor disarms, then she pivots straight into a clear, relevant value prop.
Example 4: LinkedIn comment + DM combo
Comment on a RevOps post about pipeline hygiene:
"‘Pipeline hygiene’ is such a polite way to describe deleting 60% of deals that should have been closed-lost three months ago. Curious how you’re handling that today."
Follow-up DM:
"Had to comment on your post, it’s rare to see someone admit the forecast is held together with color-coding and optimism. If you’re ever exploring ways to make that less painful, happy to share what we’re seeing other RevOps leaders do. No pitch deck, I promise."
How This Applies to Your Sales Team
Let’s get practical. How do you roll this out across an SDR org without chaos?
For SDR/BDR leaders
- Update your enablement: Add a module on using humor responsibly. Include the 3R Framework, your guardrails, and approved examples.
- Pick owners: Assign one SDR and one marketer as "tone captains" to review new humorous ideas before they go live.
- Align on metrics: Make sure ops and leadership agree on how you’ll judge success, opens, replies, meetings, and ultimately pipeline.
For frontline SDRs
- Start with one humorous element in one sequence.
- Make sure you understand the pain you’re joking about. Read your persona research, listen to call recordings, talk to AEs.
- Keep your humor short and punchy, one line. If you’re writing a paragraph, it’s too long.
- Pay attention to replies. If you start seeing, "Love this email" or "Appreciate the candid note," you’re on the right track.
For marketing and RevOps
- Centralize learnings: Capture results from humor A/B tests in a shared dashboard.
- Protect deliverability: Make sure you’re not using spammy patterns (excessive caps, emojis, misleading hooks) in the name of being funny.
- Feed insights back into brand: If a certain style of humor consistently performs, self-deprecating, dry, or playful, consider how it informs broader brand voice.
Where SalesHive fits
If this all sounds great but your team is already maxed out just getting basic outreach out the door, this is where partnering with specialists helps.
SalesHive combines:
- List building, tight ICP-aligned lists, so humor is landing with the right people
- Cold calling & email outreach, SDR teams trained on using pattern interrupts and personality in a disciplined way
- AI-powered personalization (eMod), transforming templates into hyper-personalized emails using public data, then wrapping that context in light, on-brand humor
- Testing & reporting, multivariate A/B tests, open-rate sampling, and detailed performance dashboards
Because SalesHive has already helped clients book over 100,000 meetings across hundreds of B2B companies, they have a deep library of what actually works, including humorous copy that’s been pressure-tested across industries.
Conclusion: Make Them Smile, Then Make Them Buy
Humor in B2B sales outreach is not about being the funniest vendor in the inbox. It is about being the most human.
The data is clear: buyers remember and prefer brands that make them feel something. Humor, used with relevance, respect, and restraint, is one of the fastest ways to cut through serious, same-sounding noise and start real conversations. It can lift open rates, reply rates, and meetings booked, but only if you pair it with smart targeting and a clear value proposition.
If you take nothing else from this guide, take this:
- Start small: one sequence, one joke.
- Test it like any other variable.
- Keep what moves the numbers, ditch what doesn’t.
And if you want help turning all of this into a repeatable, scalable outbound engine, with SDRs, targeting, personalization, and testing baked in, that’s literally what SalesHive does every day.
Make your prospects smile. Then make it easy for them to say yes.
📊 Key Statistics
Expert Insights
Humor only works if it is rooted in a real buyer insight
The best sales humor is basically an inside joke about your prospect's world, their tech debt, their approval process, their never-ending QBR slide decks. Before you write anything funny, get crystal clear on the everyday annoyances your ICP deals with and build your joke around that shared reality. If a stranger outside the industry would laugh, but your buyer would shrug, you are not there yet.
Treat humor like seasoning, not the main course
In B2B outreach, you do not need a comedy monologue; you need one or two lines that make your prospect think, 'Okay, this person gets it.' Add humor to subject lines, openers, or PS sections while keeping the core value prop razor-sharp. If you are spending more time wordsmithing the punchline than clarifying the problem you solve, you have flipped the priorities.
Pair humor with personalization to protect reply rates
Random jokes feel gimmicky, but a quick, witty nod to a prospect's company news or recent LinkedIn post feels human and thoughtful. Use your research, or an AI tool like SalesHive's eMod, to pull in specific context, then layer in light humor around that detail. This combination consistently outperforms generic 'funny' templates and keeps you away from spammy-feeling copy.
Always define your red lines before you let SDRs experiment
If you encourage humor without guardrails, you will eventually get a joke that makes legal spit out their coffee. Put in writing what is off-limits (politics, personal traits, sensitive events, anything punching down) and share concrete examples of 'safe' vs 'too far.' That way SDRs have room to play inside a clearly marked box rather than guessing where the line is.
Measure humor like any other tactic, not like a vibe
Humor is only 'good' if it moves numbers. Set up A/B tests where the only difference is one humorous element, a subject line pun, a playful opener, a funny CTA, and track opens, replies, positive responses, and meetings booked. Keep the winners, kill the losers, and build a library of proven humorous snippets your whole team can reuse.
Common Mistakes to Avoid
Using generic or forced jokes that are not tied to the buyer's world
Random memes or dad jokes make you look like you are trying too hard and can cheapen your brand, especially with senior decision-makers who are busy and skeptical.
Instead: Anchor every joke in a real insight about your ICP's day-to-day, approvals, tech stack chaos, endless meetings, so the humor signals empathy and expertise, not desperation.
Punching down at the prospect or their company
If your joke implies the buyer is incompetent or their current solution is stupid, you put them on the defensive and kill any chance of open conversation.
Instead: Aim the humor at the shared enemy (broken processes, clunky tools, absurd corporate bureaucracy) or at yourself as the salesperson, never at the person you are trying to win over.
Letting untested humor go out at full volume
Rolling a new tone across thousands of contacts without testing is how you stumble into spam folders, low reply rates, or social screenshots of your email for the wrong reasons.
Instead: Pilot humorous variants on small, well-defined segments first, measure impact against control cadences, and only scale the versions that clearly outperform on open and reply rates.
Ignoring cultural and industry context
What plays well with SaaS marketers in Austin may land horribly with CFOs in Germany or healthcare compliance leaders in New York.
Instead: Tier your humor by segment, more playful and informal for creative or tech audiences, more subtle and dry for regulated or conservative industries, and localize references where needed.
Thinking humor can rescue bad targeting or a weak offer
Jokes do not fix irrelevant messaging; they just make irrelevant messaging more annoying and more likely to get marked as spam.
Instead: Get your ICP, list quality, and core value prop dialed in first, then layer humor on top as a differentiator once you are sure you are talking to the right people about a real problem.
Action Items
Define a simple humor style guide for your sales org
In one page, outline what is allowed (light self-deprecation, shared pain jokes, mild wordplay) and what is off-limits (politics, personal characteristics, dark topics). Share 'good' vs 'bad' examples so SDRs have clear guardrails.
A/B test humorous subject lines on a small but high-fit segment
Take one proven campaign, create a humorous subject line variant that is still relevant to the offer, and test it on 50-100 contacts. Measure open, reply, and positive response rates before rolling it out wider.
Add a single humorous pattern interrupt to your cold call opener
Equip reps with 1-2 optional lines (for example, asking if they caught the prospect at a 'terrible time or just a bad one') and let them test these for a week, tracking connection-to-meeting conversion.
Build a shared 'humor snippets' library in your sales playbook
Collect subject lines, openers, PS lines, and call one-liners that A/B tests show are working. Store them in your enablement hub or CRM and tag them by persona/industry for easy reuse.
Leverage AI tools to personalize humorous outreach at scale
Use an AI personalization engine like SalesHive's eMod to pull in prospect-specific context (recent posts, company news) and then wrap it in light humor, ensuring each message feels researched, not robotic.
Review and update KPIs to capture the impact of humor
Beyond opens and replies, track meetings booked, opportunity creation, and time-to-opportunity on sequences where humor is present so you can quantify its influence deeper in the funnel.
Partner with SalesHive
On the email side, SalesHive’s AI-powered eMod engine turns templates into highly personalized messages at scale, pulling in prospect and company context and then weaving in light, relevant humor that still feels on-brand. That combination of personalization plus personality is why many of their campaigns see double-digit lifts in open and reply rates, and in some cases 18-34% higher open rates and 22% more meetings when humor is used strategically. For phone and multichannel outreach, SalesHive’s US-based and Philippines-based SDRs are trained on proven call openers, pattern interrupts, and follow-up scripts that use humor to disarm prospects without derailing the conversation.
Because SalesHive operates as an extension of your team, without annual contracts and with risk-free onboarding, they can help you test humorous messaging safely, run multivariate A/B tests across large volumes, and quickly standardize the lines that actually move the needle. If you want to explore humor in your sales outreach without gambling your pipeline on guesswork, SalesHive is set up to help you do it methodically and at scale.
❓ Frequently Asked Questions
Does humor really work in B2B sales outreach, or is it just a marketing gimmick?
Humor absolutely works in B2B when it is done with intent. Multiple studies show that humorous ads increase brand connection, affinity, and engagement among business decision-makers, and that people are significantly more likely to open emails with funny subject lines. For sales teams, that translates into more opens, more replies, and more meetings, as long as the humor is relevant to the buyer's world and paired with a real value proposition.
Is it risky to use humor with enterprise or senior executives?
It can be if you go too informal or edgy, but light, respectful humor is usually safe even with C-level buyers. Senior execs are just as tired of stiff, buzzword-filled emails as everyone else. A wry comment about endless steering committees or forecast meetings can actually signal that you understand their reality. The key is to keep it subtle, never joke about the person's competence, and quickly pivot to a serious business value.
Where is the best place to add humor in a cold email?
The lowest-risk, highest-impact places are the subject line, first sentence, and PS. A playful subject line can lift opens, a quick wink in the opener can humanize you, and a funny PS (for example, referencing bad sales emails you both get) can leave a positive impression. The core of the email, your problem statement, social proof, and CTA, should stay clear and straightforward.
How do we keep SDRs from crossing the line with jokes?
Start by writing a short humor policy with clear red lines and examples. Run a quick enablement session to review good vs bad outreach, and require new humorous copy to go through a manager or marketing for the first few weeks. Over time, build an approved library of subject lines and snippets that reps can mix and match rather than inventing everything from scratch.
Can AI help us write humorous outreach, or will it just make things sound fake?
AI can help, but only if you feed it real context and keep a human in the loop. Tools like SalesHive's eMod use AI to research prospects and generate personalized drafts that feel like a human did the homework. From there, SDRs can add a light joke or tweak the tone. Fully automated 'funny' emails with no human edit often feel off and can hurt reply rates, so use AI as a co-pilot, not a replacement.
How do we measure whether humor is actually improving our outbound results?
Treat humor like any other variable in your sales motion. Run controlled A/B tests where the only difference between two variants is the humorous element, then compare open rate, reply rate, positive reply rate, and meetings booked. Tag opportunities in your CRM that originated from humorous sequences so you can track pipeline and revenue impact over time. If it does not move the numbers, rework the joke or retire it.
Is humor appropriate for regulated industries like finance or healthcare?
You need to be more conservative, but you do not have to be humorless. Instead of big jokes or memes, use subtle, dry humor and focus on universally relatable situations, compliance training overload, never-ending audits, complex approval chains. Always run new messaging by legal or compliance, and keep your humor squarely on processes and systems, not on patients, customers, or sensitive topics.
What if our brand voice is serious – will humor confuse prospects?
Your brand can still be serious and trustworthy while having the occasional human moment. Think 'one light touch per email or call' rather than a full comedic rebrand. Align with marketing on tone (for example, 'straightforward with a dry wit') and use the same style across channels. Most prospects are pleasantly surprised when a serious, expert brand also shows a bit of personality.