Guide: How to Run Prospecting Days to Book Millions in Pipeline

Including a Starter Kit for Organizers

Read time: 27 min

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Welcome to a new 🔒 subscriber-only edition 🔒 of my weekly newsletter of Outbound Kitchen. Each week I dive into reader questions about scaling outbound and making it your #1 growth engine. For more: Live Outbound Classes | Podcast

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Excited to be back with paid newsletters and for this new one let's focus on How to Run Prospecting Days to Book Millions in Pipeline.

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The #1 reason sales teams fail?

An empty pipeline.

Jeb Blount said it, and he’s right.

For most B2B SaaS teams, building a predictable pipeline still feels like trying to push a truck up a hill.

Maybe you already tried scaling outbound.

Maybe you bought fancy tools or followed a framework you saw on LinkedIn.

And still, pipeline’s not where it should be.

Revenue misses. Pressure goes up. People start blaming each other.

Yeah, we’ve all been there.

But what if there was one simple play you could run right now to fix it?

Not a 90-day experiment. Something quick, proven, and easy to launch.

It’s called a Prospecting Day.

A full-company sprint focused only on one thing:

Booking meetings. Creating pipeline. Closing the gap.

Just one Prospecting Day can generate millions in pipeline, and the most importantly: build a strong outbound culture.

I’ve seen it. I’ve done it.

In this guide, I’ll show you how to run your own, step-by-step:

1. Selling the Idea Internally (getting buy-in with executive messaging & ROI)

2. Preparing Your First Prospecting Day (timeline, checklists, enablement, templates)

3. Executing on the Day (agenda, Slack rituals, energy boosters, leaderboards, remote vs. in-office tactics)

4. After the Day (tracking results, celebrating wins, follow-up, Reporting ROI to the C-Suite)

Let’s get cooking.

1. Selling the Idea Internally (Buy-In & ROI)

Don’t just throw a “Prospecting Day” on the calendar and hope people show up. If your leadership team and the rest of your go-to-market crew aren’t into it, it won’t work. You’ve got to make them care.

Here’s how:

Start with the problem: no pipeline = no revenue.

Be blunt. Tell them straight up: “Hey, we’re not gonna hit our numbers unless we fix this now.”

Use numbers to make it real. Something like:

“Our Q2 pipeline is only at 1.5x our target. We’re way below the 3–5x we need. If we don’t act now, we’ll miss our ARR goals.”

This isn’t about being dramatic. It’s about urgency. People don’t move unless they feel the pain.

Frame it as a Company-Wide or GTM Sprint

Emphasize that a Prospecting Day is a one-day “sprint” where everyone helps build pipeline.

• If you’re early-stage, make it company-wide.

• If you’re bigger (Series B+), make it GTM-wide.

Sales, Marketing, CS, even Product and Engineering, they can all help. Maybe they give warm intros. Maybe they clean up account lists. Maybe they just boost the energy. Everyone has a role.

And let’s be real: most teams rely too much on inbound. This helps fix that.

Calculate the ROI

Be clear about the expected outcomes and ROI. For instance, “If each rep books 3 meetings on Prospecting Day and our historical win-rate is 20%, one day’s effort could yield X new deals worth $Y in ARR.”

Use past data or benchmarks (like ServiceNow’s Prospecting Days adding ~$2M pipeline) to legitimize these projections.

Outline a realistic goal (e.g. “Add $2M in pipeline in one day” or “Book 50 qualified meetings”) and how that feeds the revenue engine.

Secure Executive Sponsorship

Get a visible executive champion (CEO, CRO, Founder) to back the initiative publicly. Leaders should communicate that Prospecting Day is a top priority, not a sales contest. Have the CEO send an announcement or talk about it in All-Hands meetings to lend weight. Executive participation on the day (joining kickoff, providing shout-outs, or even calling a few prospects) shows that leadership is “all in.”

Craft an Inspiring Pitch

When introducing the idea, be transparent about challenges and bold about the solution.

Clearly state: Why you need a Prospecting Day (e.g. pipeline shortfall, new product launch, end-of-quarter push), What it is (a one-day coordinated blitz to contact prospects/customers and set meetings), and How it will work at a high level.

Show What “Great” Looks Like

Share quick case studies or hypothetical outcomes to make it tangible.

For example,

• At Kahua, one Prospecting Day added $3M to pipeline in March 2025.

• “At [Company X], one Prospecting Day engaged 25% of target accounts, booked 78 meetings, and added $2.2M to pipeline”

Paint a vision of success and maybe read a mock “day-after” email celebrating wins (I’ll provide a template later). This future-casting helps everyone visualize the payoff and gets them excited.

Address “Pipeline vs. Revenue” Skeptics

Preemptively tackle the common objection that “pipeline doesn’t pay the bills, revenue does.” Acknowledge it but counter with logic: without pipeline, you’ll have no deals to close in coming quarters. Reinforce that this is about creating future sales opportunities. Also mention that Prospecting Day isn’t just about quantity, it will be quality-focused, aimed at your ICP (ideal customer profiles), increasing the chance these meetings convert to revenue.

Here's an example:

Internal Announcement Template

Once leadership is on board, send a company-wide (or GTM team) announcement to kick things off.

Here’s a template you can adapt:

Subject: Announcing Prospecting Day

Hi team,

We have an important initiative coming up: on [Date], we’re hosting our first Prospecting Day. 
This will be a one-day company-wide sprint to generate new pipeline and book meetings with future customers. 

Why? Our pipeline coverage is below target, and we have an opportunity to turn things around together.

What to expect: 

Everyone in the company (or GTM team) will play a role – from making calls and sending emails to supporting with research and cheerleading. We’ll have a full agenda (morning kickoff, scheduled call “sprints”, live leaderboards, and an end-of-day celebration). Prizes will be awarded for top contributors, and bragging rights are on the line!

Why do this: 

Pipeline is the lifeblood of our business. With a focused effort, we aim to add at least $[Target] in pipeline in one day. That could translate to significant revenue next quarter. Plus, it will be a great team-building experience and a chance to sharpen our outreach skills.

Next steps: 

Managers will soon share more details, schedules, and how to prepare (including training, target account lists, and scripts). For now, mark [Date] as Prospecting Day – Calendar Blocked ✅. No meetings or demos – just focused prospecting energy.

Let’s rally together to make this a huge success. More info coming soon. Get excited!

(Feel free to reply here or ask any questions in #prospecting-day channel.)

– [Your Name] (on behalf of the Exec Team)

This message sets a clear expectation, explains the why, and starts building energy. The key is to ensure everyone understands the importance and is on board from the start.

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2. Preparing Your First Prospecting Day (Timeline, Checklist, Enablement, Templates)

A successful Prospecting Day relies heavily on preparation.

Preparation can take several weeks of planning, coordination, and enablement to ensure the day runs smoothly.

This section provides a detailed timeline and checklist, along with templates to get your team ready.

2.1 Establish the Essentials (Owner, Date, Goals)

Assign an Owner and Core Team

Designate a single threaded owner for Prospecting Day, often a sales leader or revenue ops person who loves project management.

This person will coordinate all prep activities. If possible, assemble a small task force (Sales Manager, SDR leader, Marketing rep, Sales Ops) to divide prep tasks. Make roles clear (e.g. list building, comms, tech setup, prizes).

Set the Date and Block Calendars

Pick a date 3–4 weeks ahead. Mid-week works best.

And make it a real full-day event. Not “oh I have a meeting at 2PM.”

Tell people: No internal calls. No customer meetings. Just this.

Get it in everyone’s calendar early with a big “BUSY” block. This is non-negotiable.

Define Target Outcomes

You need a clear target. Otherwise, how do you know if it worked?

Example:

• “Book 50 meetings.”

• “Add $2M to pipeline.”

• “Engage 30% of untouched Tier-1 accounts.”

• “Book 20 meetings with the retail industry.”

• “Book 30 meetings with CMOs.”

You can also track stuff like:

• Conversations started

But the main goal should be clear, simple, and exciting. You want a number people can chase.

Choose Who’s In (Spoiler: It Shouldn’t Just Be Sales)

Decide which teams will actively participate. Sales (AEs, SDRs/BDRs) are obvious, but involve:

• Marketing (for content & data support)

• Customer Success (to call into existing accounts for upsells or referrals)

• Leadership and Execs (to provide air cover and possibly reach out to their peers at target accounts).

Make it clear everyone’s invited, including engineers or others who might take an hour to send personal notes to prospects in their network.

Plan Communications and Hype

Plot out an internal comms plan leading up to the day. This includes teaser announcements, reminders, and training sessions.

For example, schedule a All-Hands prep call a few days prior to review the plan (more on that below). Create a dedicated #prospecting-day Slack channel for ongoing chatter and updates. Use this channel pre-event to drip out motivational content: share the agenda, tips, leaderboards previews, etc.

Secure Prizes or Incentives

Decide on any awards for top performers or fun spot prizes. They can be simple (company swag, a day off, a trophy, gift cards, or even just bragging rights with a funny title).

Having prizes for categories like “most meetings booked”, “biggest opportunity” etc., adds excitement.

Announce what these prizes are before the day so people know what they’re competing for.

Logistics Check

If using specific tools (auto-dialers, video meeting links, Salesforce campaigns, etc.), ensure they are set up and tested.

• If the team is in-office, book a room or area with plenty of phones and good Wi-Fi.

• If remote, ensure everyone has Zoom/phone access and the Slack channel ready.

Also decide how you will keep score (shared Google Sheet, a live dashboard, a whiteboard in office, see Section 3.2).

CRM & Dashboard Tracking

Ensure your CRM (Salesforce, HubSpot, etc.) is the central source of truth for tracking results with Campaigns. Create a dashboard or report in the CRM to monitor Prospecting Day metrics in real time (calls, meetings, opps created). Use the CRM to tag all activities from that day for easy reporting. A CRM dashboard visible to all can function as a leaderboard as well. Use your CRM to measure what’s working and identify areas to adjust.

This mirrors best practices where everything from an owner and date to follow-up emails and even the next event are planned in advance .

2.2 Timeline: 2-4 Weeks to Prep

Below is a sample timeline to prepare your first Prospecting Day. Adjust based on your org’s size and speed, but the idea is to work backwards from the date:

4 Weeks Before Day (Kickoff Planning)

• Secure leadership approval and budget (if needed for prizes or tools).

• Announce the Prospecting Day date to all relevant teams (use the template above or company meeting).

• Owner begins coordinating with Sales/Marketing Ops to start pulling target lead lists and any data enhancements needed.

• Create the #prospecting-day Slack channel and invite everyone. Post a welcome message about using this channel for updates and fun (e.g. “Welcome to Prospecting Day central! Stay tuned for tips and updates here.”).

3 Weeks Before

Prospect List Building

Define which prospects or accounts will be targeted. Pull reports of stagnant opportunities, high-fit prospects not yet contacted, and customer expansion targets. Clean and segment these lists (more on list prep below). Assign owners for each list segment (e.g. SDRs get new logos, AEs get dormant opps, CSMs get upsell calls). Ensure no overlap and that each rep has a clear book of people to contact.

All-Hands Prep Meeting Scheduled

Put on the calendar a company prep meeting for 1 week before the event. In this meeting, you’ll explain the full game plan to everyone, set expectations, and get folks pumped. Start assembling a simple slide deck (cover the Why, How, What as Ralph Barsi suggests).

2 Weeks Before

Team Training & Role-Play

Host enablement sessions. For sales reps, do a call blitz training or refresher: how to handle cold call openers, navigate gatekeepers, etc. For non-sales participants, explain how they can help (e.g. Marketing can share relevant content, Engineering might send personalized “technical outreach” emails to ex-users, etc.). If some team members are nervous, run role-play exercises (possibly using ChatGPT as a practice buddy).

Dry Run (Optional but Recommended)

Have a mini one-hour prospecting simulation with a few team leads. This helps catch snags early (e.g. CRM issues, phone system load, people unsure of scripts). It’s especially helpful for leaders new to this format, to practice managing rounds and answering rep questions on the fly.

List Finalized & Enriched

By now, the prospect lists should be near final. Double-check contact info. Fill missing phone numbers or emails via tools like ZoomInfo/Lusha if available. Ops can help enrich records with latest intel (e.g. recent news on target companies). If you have closed lost opportunities, dig up those threads for context. Prioritize quality over quantity – better to have slightly smaller, well-researched lists for higher conversion.

1 Week Before

• All-Hands Prep Rally: Hold the pre-event meeting with all participants. Present the slide deck covering:

  • Why we’re doing this: reiterate challenges (pipeline gap, etc.) and goals.

  • How it works: the date, the agenda for the day (coming in Section 3), who’s doing what, how to use the Slack channel, how leads are distributed, etc.

  • What we expect: outline targets and hype up the competition. Announce prize categories. Remind everyone it’s all-day and “100% focus”.

  • Get a senior exec to deliver a pump-up pep talk here. Solicit any Q&A so concerns are addressed now.

  • If you have any cheat sheets (quick reference guides on product info, talk tracks, etc.), distribute them now so reps can study.

• Prospect Outreach Warming: In the days leading up, consider “warming up” some prospects:

  • Have reps send brief pre-emails to important targets a few days ahead: e.g. “Hey, will try giving you a call on Thursday regarding XYZ – hope to connect.” This can soften the cold call and even yield some scheduled calls in advance. As Ralph Barsi advises, pre-emptive emails like “How does [Prospecting Day date] at 9:30am or 1:30pm work for a quick call?” give prospects an easy out.

  • Executives can reach out to their network for intros: e.g. if a founder is connected to a CEO you want to reach, have them send a friendly heads-up or intro email. Warm introductions drastically improve connect rates.

  • Marketing can run a quick awareness touch (like a targeted LinkedIn ad or a nurture email) to the target account list, so your company is on their radar that week.

• Finalize Scripts & Tools: Lock in the cold call scripts. Print them out or pin in a shared doc for easy access on the day. Ensure the CRM or tracking sheet is ready for real-time input. Have a dashboard or scoreboard mechanism ready (even if it’s a simple Google Sheet tallying each rep’s calls/meetings). Test any tech (dialers, Zoom links for group huddles, etc.) now.

• Logistics & Morale Boosts:

  • If in-office, arrange catering for breakfast and lunch on Prospecting Day.

  • If remote, consider sending everyone a $15 UberEats voucher or company-expensed lunch – removing any friction so they can focus on dialing.

  • Little perks like branded T-shirts (“Prospecting Day Brigade”) or energizing snacks can also set a positive mood. These were effective in one example where Marketing made “killer swag” (hoodies, mugs) that reps proudly used during the day. Not required, but fun touches.

• Reminders: As the day approaches, keep the excitement up. Post a countdown in Slack (e.g. “3 days to Prospecting Day!”). Share daily tips or success stories from past prospecting wins. Ensure every participant’s manager checks in that they’re clear on their tasks and ready.

By EOD before Prospecting Day, the entire company should know what’s happening tomorrow, why it matters, and feel equipped to crush it.

2.3 Tools & Templates for Preparation

Preparation isn’t just planning, it’s also creating assets and using tools to empower the team. Here are practical “tools” you can deploy:

Prospecting Day Agenda (Run-of-Show) Template:

Create a visual agenda that can be shared. For example, a simple agenda could be:

You can adapt timing (some do four rounds, some five shorter rounds) but build in short breaks. No one can cold-call non-stop for 8 hours straight. A typical structure is 1-hour call blocks with 30-min breathers. Include a proper lunch break. Plan a celebratory happy hour (virtual or in-office) at day’s end. Share this agenda in advance so everyone knows the rhythm.

Internal Comms Templates

Aside from the initial announcement, prepare a reminder message the day before (e.g. “Tomorrow is Prospecting Day! Quick reminders: be logged in by 8:45 for kickoff, have your target list and scripts ready, and most of all, bring the energy. Let’s do this!”). Also prepare the day-after follow-up email to send results (we’ll cover content for that in Part 4).

Objection-Handling Flashcards

A fun prep idea: create flashcards of common objections (“Not interested”, “Too busy”, “Send me info”, “No budget now”) and have reps practice quick responses. This could even be a short segment in the all-hands prep call: a manager poses an objection and a rep practices a response live. The better prepared reps are to handle “can you email me something?” or gatekeeper screens, the more confident they’ll be on the day.

Prospect Research Docs

For top accounts, have marketing or SDRs compile one-page dossiers: key contacts, LinkedIn bios, recent news, known pain points. These help personalize outreach. Even better, share an “Ideal Customer Profile & Personas” cheat sheet that outlines typical buyer challenges and how your solution helps (an example is making a table of persona vs. their pain vs. your value prop). Reps can tailor their pitch knowing the persona’s likely concerns.

Cheat Sheet for Organizers

As the organizer, keep your own checklist or “run sheet” for the day. This includes the schedule, a list of whom to call at each break for updates, a reminder of what needs to be announced when (e.g. “9:00 – send Slack message to begin Round 1; 10:00 – post Round 1 results in channel; 4:00 – gather final stats for wrap-up”). Essentially, script your facilitation moves so you can focus on energizing the team and not forget any steps.

You'll find the cheat sheet below in the paid section.

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🔒 Wait! Want the rest of the guide to Run Prospecting Days to Book Millions in Pipeline?

Here’s a quick taste:

• Prospecting Day Starter Kit: including: the Cheat Sheet for Organizers Email templates to use, and a Mini One-Pager: Reporting ROI to the C-Suite

• Part 3: Executing on Prospecting Day (Agenda, Energy, Comms & Competition)

• Part 4: After the Day: Tracking Results, Celebrating Wins, Follow-Up, and Reporting ROI to the C-Suite

🔓 Want the full guide?

It’s for paid subscribers only, but you can start a 7-day free trial now and get everything (plus the Cheat Sheet + email template).