Sales Intelligence Platform

Intelligent recommendations that move deals.

Your CRM holds every win, every loss, every pattern your best rep has ever created. Sidekick learns from it and creates personalised plays for every rep, on every deal.

So your whole team sells like your best closer.

# sidekick-intelligence
6 members
S
Sidekick APP 9:02 AM
in #deal-northstar
Strong match — 9/10
This type closes fastest when demo happens within 5 days. You're at day 3. Book today.
S
Sidekick APP 11:34 AM
in #deal-fieldstone
⚠️ At-risk deal
No activity for 9 days. 8/10 deals that stalled here were lost. Schedule follow-up now.
S
Sidekick APP 2:15 PM
in #deal-runway
Move fast on this one
E-commerce deals close in 14 days or not at all. Single decision maker identified. Push to proposal.
S
Sidekick APP 4:48 PM
in #deal-acme
Objection incoming
"Too expensive" surfaces in 68% of deals at this stage. Lead with ROI calc — closes at 2×.
S
Sidekick APP 9:02 AM
in #deal-northstar
Strong match — 9/10
This type closes fastest when demo happens within 5 days. You're at day 3. Book today.
S
Sidekick APP 11:34 AM
in #deal-fieldstone
⚠️ At-risk deal
No activity for 9 days. 8/10 deals that stalled here were lost. Schedule follow-up now.
How it works
From your CRM to the right play.
Two inputs. One living playbook. Plays in Slack.
HubSpot
Closed deals
Won + lost history
Analyse
ICP groups
Segments identified
Industry · size · location
Generate
Playbook
Win patterns
Multi-thread by day 7 · 91%
Demo within 5 days · 74%
Objections
"Too expensive" → ROI · 2×
Risk signals
No activity 5+ days · 80%
HubSpot
Open deals
Live pipeline
Match
Slack
Plays delivered
Northstar · 15 mins
Lead with ROI. Champion not identified yet.
HubSpot
Closed deals
Won + lost history
HubSpot
Open deals
Live pipeline
Playbook
ICP groups
B2B SaaS · USFintech · UKE-comm · US
Win patterns
Multi-thread by day 7 · 91%
Demo within 5 days · 74%
Objections
"Too expensive" → ROI · 2×
Risk signals
No activity 5+ days · 80%
Slack
Plays delivered
Northstar · 15 mins
Lead with ROI. Champion not identified yet.
ICP Playbooks

Not one playbook. One per buyer type.

Each ICP segment gets its own structured playbook extracted from your closed deals in that segment.

B2B SaaS · 50–200 · US
48% of wins · avg. $18k · 22 day cycle
Win pattern
Multi-thread by day 7 91% WR
Demo within 5 days 74% WR
Top objection
"Too expensive" → ROI calc 2× close
Risk signal
No activity 5+ days at proposal → 80% loss rate
Financial Services · 200–500 · UK
31% of wins · avg. $42k · 44 day cycle
Win pattern
Legal by stage 2 68% WR
Compliance-first pitch 61% WR
Top objection
"Security concerns" → SOC2 + case study 3× close
Risk signal
Proposal before security review → 71% loss rate
E-commerce · 10–50 · US
21% of wins · avg. $8k · 11 day cycle
Win pattern
Close within 14 days 83% WR
Single decision maker 91% WR
Top objection
"Not the right time" → create urgency lose if ignored
Risk signal
Past 14 days without close → 89% loss rate
The playbook

A living sales playbook built from
your best reps' instincts.

Your best reps have an instinct. Built from hundreds of deals, wins, losses, and patterns absorbed over years. They know which buyers close fast. They know what objection is coming before it's raised. They know exactly when to push and when to wait.

That knowledge lives in their heads. And walks out of the door with them.

Sidekick recreates it using patterns derived from your CRM. When to multi-thread and who to bring in. When to follow up and when to back off. Which objections are coming and exactly what works against them. Your ICP segments, win patterns, and stage timing, organised, specific, and updated automatically every time you close a deal.

And then it keeps learning from your deals as you close more. This knowledge feeds your processes. And helps your reps close faster.

Acme Corp Sales Playbook
Updated today
Sections
ICP
Win Patterns
Objections
Deal Stages
Risk Signals
Who actually buys
B2B SaaS · 50–200 RevOps owner HubSpot + Slack Series A–B SDR team 3+
Multi-threaded
87%
Champion ID'd
91%
Demo in 5 days
74%
Pipeline Co-pilot

Every rep sells like they've closed this buyer before.

Sidekick delivers three types of intelligence in Slack — before the meeting, when a deal is created, and as deals progress.

Meeting prep
S
Sidekick APP 8:45 AM
Hey Jamie — you have a call with Northstar in 15 minutes. Here's what you need to know.
The deal Northstar is at proposal stage. They're a B2B SaaS company, 120 employees, RevOps-led buying process. This is your Segment A — your strongest converting ICP. Average cycle for this segment is 22 days. You're at day 18.
Who's on the call Jamie Miller (VP Sales) and Sarah Chen (Head of RevOps). Sarah was added last week — a good sign. Decision makers are engaged.
What to focus on Lead with the ROI calculation you prepared. 91% of your wins in this segment had a champion identified by now — confirm Sarah is your champion and get her to vouch internally. Push for a sign-off timeline today.
Watch out for "Too expensive" comes up in 68% of deals at this stage. Reps who lead with feature justification lose this objection. ROI framing closes at 2×.
Deal Coaching
S
Sidekick APP 2:12 PM
New deal created — Runway Inc. Here's what your playbook says about this buyer type.
Who they are E-commerce company, 35 employees, US-based. Founder-led buying process — you'll likely be speaking directly to the decision maker. Fits your Segment C, which accounts for 21% of your wins.
How this segment buys Fast or not at all. Your average cycle here is 11 days. Deals that drift past 14 days close at 89% loss rate. Don't let this one sit — get to a demo within 3 days and push to proposal before day 8.
What wins deals here ROI-first framing, not feature walkthroughs. Founders want to know the payback period. Keep it simple and move fast — urgency is your friend in this segment.
Common objections "Not the right time" — this almost always means you haven't created enough urgency. Don't accept it. Reframe around cost of inaction and push for a concrete next step today.
Live intelligence
S
Sidekick APP 4:48 PM
Multi-threading gap
#deal-fieldstone — only one contact engaged at Proposal stage.
75% of similar won deals had 3+ contacts by now. You're single-threaded into a RevOps contact. If they leave or go quiet, this deal is gone.
Add: VP of Sales, Procurement Lead — search Fieldstone on ZoomInfo →
Stalled deal
#deal-acme — no activity in 11 days. Still at Demo stage.
Similar deals that recovered from a stall had a follow-up within 3 days of going quiet. You're past that window. Every day without contact reduces close probability.
Action: Send a re-engagement email or call today. Draft a follow-up →
Buying committee
#deal-northstar — heading into Negotiation without a Finance sign-off contact.
82% of won deals in this segment had a CFO or VP Finance engaged before contracts were sent. Without them, deals stall at legal review and drag for weeks.
Missing: CFO or VP Finance — ask your champion to make the intro now.
How it works

Connect your CRM. We do the rest.

Four steps from connection to your first playbook — and recommendations on every open deal.

Step 01 · 60 seconds

Connect your CRM

Read-only OAuth. 60 seconds. We analyse your closed-won and closed-lost deals to find patterns. No deal-specific data is stored.

HubSpot supported
Step 02 · Automatic

We identify your ICP groups

Sidekick analyses your deal history and automatically identifies your buyer segments by industry, company size, and location. No manual configuration needed.

Step 03 · Automatic

A playbook generated per group

Each ICP group gets its own structured playbook — win patterns, objection handling, buying committee, stage timing, and risk signals. All derived from your data.

Step 04 · Ongoing

Plays for every open deal

Every new deal is matched to the right ICP group. Sidekick delivers the right play in Slack — before meetings, when deals stall, and when buying committee gaps appear.

Impact

What changes when every rep has the right play.

Faster time to close
Reps know the next move on every deal. No guessing, no stalling. Deals move through stages the way your best ones always have.
Higher win rate
When every rep runs the play that works for each buyer type, execution gets consistent. Consistent execution wins more deals.
Faster rep ramp
New reps don't learn by trial and error. They start with a playbook built from every deal your company has ever closed.
Sharper pipeline accuracy
Pattern matching against your historical wins tells you which deals are real. Pipeline reviews stop being a negotiation.
Closed beta

Built for mid-market sales teams. 10 spots.

We're opening Sidekick Intelligence to a small group of sales teams who are serious about fixing how they sell. A working product, with commitments to your results.

Our closed beta is limited to 10 teams so that every customer gets the founding team's full attention — and walks away with a playbook that actually works for their business.

What you get
  • A living playbook specific to how your company wins, built from your own CRM data
  • Real-time recommendations that tell every rep exactly what to do next, on every deal
  • The founding team focused on your results, not just your onboarding
  • Your use cases prioritised as we build — you shape the product
  • Beta pricing locked in for life
Is this right for you?
  • You have 100+ closed deals in your CRM — enough data to generate a meaningful playbook
  • You have an active sales team of 10 or more reps who need a consistent process
  • You're using HubSpot CRM and Slack for your internal comms
4 of 10 spots remaining
$2,495
per month · 4-month commitment
Timeline
  • Week 1 — your playbook is live
  • Week 2 — rolled out to your team
  • Weekly check-ins and reviews with the founding team
  • Direct access via Slack Connect for syncs
Apply below →
Apply

Tell us about your team.

We review every application personally. Week 1, your playbook is live. Week 2, it's rolled out to your team. You'll hear back within 2 business days of applying.

We review every application personally. You'll hear back within 2 business days.