Sales Onboarding Hub

Below is your week-by-week schedule for your first four weeks — every session, exercise, and check-in mapped out. Week 1 builds the foundation (TLDR, the audience, the pitch). Week 2 is bootcamp on the tools and systems. Week 3 is pitch prep — teach-back, reverse demo, and shadowing live calls. Week 4 you activate your book of business and run your first solo call. Pair this with your Role Expectations Slack canvas, which covers your role definition, 30/60/90 plan, deliverables, and success criteria — that's the what. This is the how: what you'll actually be doing day-to-day to get there.

This schedule is subject to change. All live sessions are pre-scheduled on your calendar. You may also see additional 1:1s added to your calendar with folks relevant to your specific role.

LIVE Live session ASYNC Self-paced HANDS-ON Exercise

Week 1 — Revenue Team Foundations

▾

Goal: Understand TLDR's business, audience, and value prop.

Day	Session	Format	Lead
Mon	Day 1 orientation Company orientation, mission, key people, benefits	LIVE	Elyse
Mon	Manager welcome Welcome, intro, expectations	LIVE	Manager
Mon	Buddy intro coffee Break the ice, get to know each other, welcome to TLDR	LIVE	Buddy
Tue	Revenue team overview How the revenue team is structured, key metrics, current focus	LIVE 1 hr	Val
Mon–Fri	Self-study: Resources tab Work through the Resources tab on your own time throughout the week. This is how you'll get to know TLDR, the business model, our audience, the sales motion, and the tools you'll be using every day.	ASYNC	Self-paced
Wed	Audience & portfolio SME Which newsletter for which advertiser, vertical performance, ICP per newsletter	ASYNC LIVE	Pri
Thu	Curated call library Watch curated list of Attention recordings. See Exercises tab.	HANDS-ON	Self-paced
Fri	Sales motion SME Pitch, value prop, discovery, objections, proposal	ASYNC LIVE	Marpo
Fri	Win/loss autopsies Read 1 closed-won + 1 closed-lost summary. See Exercises tab.	HANDS-ON	Self-paced

Week 2 — Sales Bootcamp

▾

Goal: Build tool fluency through doing, not watching.

Day	Session	Format	Lead
Mon	HubSpot SME Pipeline, deal creation, activity logging, common mistakes	ASYNC LIVE	Riley
Tue	Sponsy SME Inventory, availability, booking, IO, billing contact match	ASYNC LIVE	Tyler
Tue	Full deal cycle SME End-to-end: first touch → IO → billing → handoff	ASYNC LIVE	Stef / Laura
Wed	Cowork setup + verification Install, plugins, slash commands — verified live	LIVE 45 min	Upashruti
Thu	First deal scavenger hunt + Objection handling 10-step checklist simulating a real deal setup (with buddy). Top 8-10 objections role-play. See Exercises tab.	HANDS-ON	Buddy
Fri	Amplemarket SME Sequences, enrichment, account research	LIVE	Alan
Fri	RevenueHero What it is, how we use it	ASYNC	Jiali

Week 3 — Pitch Prep + Shadowing

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Goal: Prove you can pitch. Pass the teach-back gate. Shadow live calls.

Day	Session	Format	Lead
Mon	Pre-call research on real account Research a real prospect using Cowork + ad libraries. See Exercises tab.	HANDS-ON	Self-paced
Tue	Teach-back preparation Practice run with buddy before the official presentation	LIVE	Buddy
Wed	Teach-back presentation Pitch TLDR's value prop to manager. Must pass to move to live calls.	LIVE 30 min	Manager
Thu	Reverse demo — 2 personas New hire demos TLDR ad products. Manager + 1-2 senior AEs play buyer personas.	LIVE 30 min	Manager + AEs
Thu–Fri	Shadow 3–5 live calls Shadow different AEs to see pitch variety. Take notes.	HANDS-ON	Self-paced
Fri	Lead management + prospecting Setting up sequences, working leads	ASYNC	Amplemarket SME

Week 4 — BoB Activation

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Goal: Activate your book of business. Transition to ongoing cadence.

Day	Session	Format	Lead
Mon	Account review with buddy Walk through assigned book of business using account planning template	LIVE	Buddy
Tue	First outbound sequences Set up first sequences to assigned accounts	HANDS-ON	Self-paced
Wed	First solo call + debrief First unsupervised call. Buddy shadows. 15-min debrief after.	LIVE	Buddy
Thu	Self-review Watch own teach-back recording, score self, identify 3 improvement areas. See Exercises tab.	HANDS-ON	Self-paced
Fri	Wrap-up with buddy Celebrate progress, transition to peer cadence	LIVE	Buddy
Anytime	Post-sales overview What happens after a deal closes: AdOps + AM handoff	ASYNC	Tyler

~7.05M

Total Subscribers

Newsletters

40–46%

Avg Open Rate

40%

Executive Readers

Newsletter Portfolio

TLDR

1,538,700

Mon–Fri

TLDR AI

1,046,308

Mon–Fri

TLDR IT

571,623

Mon–Fri

TLDR Data

553,706

Mon & Thu

TLDR Dev

457,641

Mon–Fri

TLDR Fintech

447,091

Mon & Thu

TLDR Product

411,954

Tue & Fri

TLDR InfoSec

402,976

Mon–Fri

TLDR Founders

370,138

Mon–Wed–Fri

TLDR DevOps

337,692

Mon–Wed–Fri

TLDR Marketing

312,842

Mon–Fri

TLDR Design

307,626

Mon–Fri

TLDR Crypto

290,898

Mon–Fri

Subscriber counts from Metabase — May 2026

Placement Types

Primary

Top placement. Longest copy, company logo, prominent CTA link. Highest visibility and click volume.

Secondary

Mid-newsletter placement. Shorter copy, company logo, CTA link. Strong engagement at lower price point.

Quick Link

Brief one-line text link in the quick links section. Lowest cost, good for brand awareness and retargeting.

Tool Stack

HubSpot

CRM — deals, pipeline stages, contacts, companies, engagement history, forecasting, rate cards.

Sponsy

Ad inventory — placement availability, bookings, campaign data, click performance, IOs.

Metabase

Subscriber analytics — audience counts, open/click rates, demographics, engagement trends.

Attention

Call intelligence — meeting transcripts, follow-up drafts, scorecard results, call prep.

Cowork / Claude

AI assistant — account research, proposal generation, call prep, competitor analysis, morning briefs.

Amplemarket

Outbound — lead and company enrichment, contact discovery, outbound sequences.

RevenueHero

Inbound routing and scheduling — lead distribution to AEs.

Google Workspace

Docs, Sheets, Slides, Calendar — shared documents, proposal templates, meeting scheduling.

Appeared.in

Ad spend intelligence — see who is sponsoring which newsletters. Use for competitive research and prospecting.

Overview deck (Google Slides)

Gamma

Presentation builder — create and share decks, proposals, and visual content.

Top Sponsors (Last 90 Days)

Company	Placements	Total Clicks
QA Wolf	57	75,338
Wispr	60	60,982
WorkOS	26	33,871
Metronome	42	24,991
Unblocked	27	21,103
Framer	31	15,179
Clerk	36	15,352
Atlassian	39	11,057
Amazon Web Services (AWS)	36	9,151
Asana	56	8,631
Microsoft Azure	37	6,776
Google	44	4,699
Sentry	42	3,923

From Sponsy — last 90 days as of April 21, 2026

The operating manual for every seller at TLDR. How we prospect, prep, qualify, pitch, close, and forecast.
Owner: Valerie Bartlett · Updated May 2026 · Reviewed quarterly

The Operating Rhythm

Why it matters: Seller habits plus company-wide rhythms — one place to see how the week, month, and quarter run.

Cadence	What	Owner	Details
Daily	Morning digest + HubSpot hygiene	All sellers	Read morning digest before first call; update HubSpot — log calls, notes, next steps.
Weekly (Mon)	TLDR Squared	All	Async team update every Monday in #team-full-time. The TLDR of TLDR — what's going on around the company.
Weekly (Wed)	Wednesday Drop	All	Async team update every Wednesday in #team-full-time. Process or policy changes in one central place.
Weekly / Bi-weekly	Manager 1:1	Rep + Manager	Standing check-in: pipeline, deals, coaching, development.
Bi-weekly	Revenue Lab	Sales team	Team learning: pitch teardowns, deal reviews, competitive intel, new product features, guest speakers. Recordings in Resources tab.
Monthly	Revenue All-Hands	Managers + Val	Full revenue team meeting — pipeline review, quota progress, strategic updates, cross-functional alignment (AEs, AMs, ops).
Quarterly	Company All-Hands	All	Full TLDR team meeting — company performance, product updates, culture, cross-team visibility.
2× / year	Team Offsites	Team	In-person gatherings — strategy, planning, relationship-building, resetting for the next half.

Rule of thumb: If a deal isn't in HubSpot by EOD, it doesn't exist. Forecast accuracy is a leading indicator of operational maturity — we measure it.

Prospecting

Objective: Build a high-quality pipeline of accounts that match TLDR's ICP and have a credible budget for newsletter advertising. Marketing Operations automates and runs the sequencing in Amplemarket; AEs provide the signal that drives the outbound sequence.

2a Find the right companies

Lookalikes to closed-won customers — easiest wins. Pull past advertisers in your vertical from HubSpot; find direct competitors via Sales Nav, ZoomInfo, or Google.
Industry maps & sponsor databases — WhoSponsorsStuff and Appeared.in for newsletter coverage; G2/Crunchbase landscape maps for vertical scans.
Filter rule: Check HubSpot ownership before adding. Territory disputes burn cycles.

2b Find the right people

Tool: Sales Navigator. Target titles: Demand Gen, Growth, Field Marketing, CMO/VP Marketing, Product Marketing, Content Marketing, Digital Marketing.

2c Request the outbound

Use the outbound request sheet and provide relevant details to the Marketing Operations team to set up sequences on your behalf.

Heads up: Make sure your email and LinkedIn Premium are provisioned into Amplemarket before requesting outbound.

Pre-Meeting Prep

Biggest change from prior playbook: You no longer manually research before every call. The system does it for you.

3a Daily Digest

Every morning in Slack you get a digest covering all your external meetings for the day. It includes deal history, past placement performance, newsletter coverage, audience fit, call history, and key talk-track notes.

3b Cowork skills for ad-hoc prep

/tldr-sales-account-research — structured intel on any company
/tldr-sales-query-builder — ad-hoc data questions
/tldr-sales-morning-brief — re-run the digest on demand

3c The four questions to answer before any call

What does the company do, and how big are they?
Who in their competitive set has run with us — and how did it perform?
Have we covered them organically? (If yes, that's a warm lever.)
What's their most likely audience fit?

Discovery & Qualification

Objective: Understand the buyer well enough to recommend a campaign that will succeed — not just one that fits their budget.

4a Discovery questions — pick 5–7 that move the deal

About them

Have you run newsletter advertising before? What worked, what didn't?
What product or offer is this campaign supporting?
Who is the target audience — title, function, seniority, company size?
What KPIs define success? Who reviews them post-campaign?

About the deal

Time frame?
Budget range? Frame it: "this helps me recommend placements you'll actually run."
Who else is in the decision? Procurement?
Where else are you advertising and how's it performing?

About next steps

What does your decision process look like from here?
When can we get on the calendar to walk through a proposal?

4b The "do not skip" criteria

A deal does not move past Discovery to Proposal until you have: confirmed budget range, confirmed timeframe, identified the economic buyer, and confirmed KPI definition. Missing any = stays in Discovery.

Reminder: Always book the next meeting on the current call. Calendar momentum is the #1 leading indicator of close rate.

The Pitch / Proposal

Objective: Show why TLDR fits this buyer's specific goal — not deliver a generic kit.

5a Use the proposal builder

/tldr-sales-proposal-builder generates a branded .pptx proposal + follow-up email from a six-field rep brief
The builder is policy-aware — pulls live rate-card pricing and refuses non-compliant overrides
Don't hand-edit the deck out of policy. Route deviations through Deal Desk in Slack.

5b Pitch flow on the call

Recap discovery — "You mentioned X audience, Y goal, Z timing."
Why TLDR vs. other newsletters — audience scale, engagement, intent
Why TLDR vs. other channels
Placement options — Primary vs. Secondary vs. Quick Links; trade-offs
Audience fit — demographic overlap with their ICP
Avg. click performance — for recommended placements, in their vertical
How we work — 7-day copy turnaround, post-campaign reporting, dedicated CSM
Recommendation + 2 alternatives — good / better / best

5c Pricing posture

We lead with value. ACV target per deal is $25K and 2+ placements. Discounts must adhere to policy or be escalated via Deal Desk.

Next Steps & Follow-Up

Objective: Close the gap between meeting and momentum. The follow-up is the deal.

6a From your side — commit on the call

Send a proposal within 24 hours
Share comparable campaign examples
Share avg. click performance for recommended placements
Send the follow-up email immediately after

6b From their side — set expectations

Internal review with manager
Build the business case
Budget approval
Signature

6c Following up

Same-day email: recap discovery, attach proposal, propose next meeting time
Task creation: create the HubSpot task before you close the call notes
The 3-touch rule: follow up 3 times across 2 weeks before marking cold

Pipeline Hygiene & Forecast

Objective: A clean pipeline is the only honest pipeline.

7a Deal stage definitions

Stage	Weight
New Deal	10%
Meeting Scheduled	20%
Meeting Completed	30%
Proposal Sent	60%
Contract Sent	90%
Closed Won	100%
Closed Lost	0%

7b Hygiene rules — every Friday

Every open deal has a future close date — no past-dated deals
Every open deal has a next step + next-step date
Every deal in Proposal+ has all criteria filled out
Stuck deals (no activity in 30 days) get pushed to Closed-Lost or Nurture

7c Forecast categories

Category	Definition
Line of Sight	Best case scenario
Commit	Most accurate read on what you think you'll land at for the quarter

What Works (Field Wisdom)

Know your client. Don't ask things a 5-min Google or the morning digest would answer.
Use social proof. Mention competitors and look-alikes who've run with us. Concrete numbers beat generic logos.
Set expectations & keep your word. "I'll follow up Thursday" → follow up Thursday, even with nothing new.
Calibrate performance promises. "I expect this to perform at category average — here's what that means in clicks and CTOR."
Ask the buyer to talk to a developer at their company. They'll find TLDR readers internally — instant credibility.

Performance Bar

Why it matters: What "good" looks like at TLDR — by role. Public bar so every rep knows where they stand.

Reference the leveling framework to understand expectations by level and role.

Ready Resources

SME video prep: Short Loom walkthroughs (portfolio, Amplemarket, lead distribution, and more) live on the tab on each SME card. Watch the relevant ones before your SME week or whenever you’re stuck on that tool — then use your live SME session to go deeper.

1.Company & Audience Foundations

The "know TLDR" set — read first.

TLDR Business Model Overview

What TLDR is, how we make money, who reads us, who sponsors us