Sample Deliverable | Northwood Creative SalesOS
Confidential — Sample
SALESOS SELLING PLAYBOOK
NORTHWOOD CREATIVE
The Operating Manual for How We Sell, Qualify & Close
PURPOSE & PHILOSOPHY
Why This Playbook Exists
Northwood did not become a sought-after partner by accident. We earned it the hard way: by listening longer than other agencies, building from real conversations instead of editorial calendars, and proving the work in pipeline rather than pageviews.
This playbook captures how we win business in a way that reflects who we are.
We are not the loudest agency in the room. We are not the cheapest. We are not the agency that pitches a 90-day content sprint on the first call. We are the agency a sharp marketing leader recommends when their friend at another company says, "our content is everywhere and nothing closes."
This playbook exists to make sure every conversation we have with a prospect feels like working with Northwood, regardless of who is on the call.
It is here to:
- Create consistency in how we attract, qualify, and close new business
- Make it easier for anyone at Northwood to participate in sales with confidence
- Ensure that every client we win is one we want to serve and one we know how to help
This is our shared operating manual for selling the Northwood way.
Our Sales Philosophy: Listen Before You Sell
Northwood does not pitch. We diagnose.
Our entire methodology starts with listening to actual sales calls. We bring that same instinct into our own sales process. The discovery call is not a pitch in disguise. It is the first piece of evidence we use to decide whether we can help.
We look for the 3 Cs:
- Conviction. We want clients who believe content is a lever for growth, not a checkbox or a vanity exercise. We do not want to spend the engagement defending the value of strategy.
- Cooperation. We want clients who are willing to give us access to their sales calls, their lost-deal notes, their pipeline reports. The work does not work without the data.
- Candor. We want clients who can tell us what is broken without flinching. We will return that candor. If we cannot help, we say so. If we think they are spending money on the wrong thing, we say so.
Sales at Northwood is not persuasion. It is pattern recognition under live conditions.
We use discovery to surface the misalignment between what a marketing team is producing and what their sales team actually needs. That misalignment is almost always there. Our job is to name it precisely so the prospect knows, in the first 45 minutes, that we see something nobody else has.
We earn trust by giving insight early and freely, not by hiding it behind a proposal.
The Northwood Sales Operating Principles
- Lead with a finding, not a framework. In every call, surface the one thing the prospect did not know about their own pipeline. That is what gets you the second meeting.
- Diagnose before you prescribe. No recommendations until you have heard at least one of their sales calls or read at least one lost-deal note. If they will not provide either, that is your answer.
- Show your math. When you say content is misaligned with sales, point to specific phrases. When you say a topic has no buying intent, show the data. We do not ask prospects to take our word for it.
- Close the gap, not the deal. Every conversation should end with the prospect understanding their gap better than they did when the call started. The deal closes itself when the gap is undeniable.
- Disqualify with the same energy you qualify. A "no" delivered with conviction is more valuable than a "yes" delivered with hope. We do not chase fit we do not feel.
- Make the next step the smallest useful thing. Do not propose a six-month retainer when a four-week diagnostic will prove the relationship.
IDEAL CLIENT PROFILE
Who We Are Built to Help
Northwood is not a fit for most companies that ask us to pitch.
We thrive with mid-market SaaS companies that have already proven the product, hit a content ceiling with their current setup, and are ready to rebuild content as a pipeline instrument rather than a marketing asset.
We are not a content factory. We are not a creative shop. We are the team you call when your inbound pipeline has gone flat, your sales team is forwarding nothing your marketing team produces, and your CFO has started using the word "vanity" in earnest.
Primary ICP: The Mid-Market B2B SaaS Brand
Firmographics
- Industry: B2B SaaS (horizontal or vertical) with average contract value above $25K
- Team size: 50 to 500 employees, with internal marketing of 4 to 12
- Revenue: $10M to $75M ARR
- Growth profile: Series B through Series D, or profitable bootstrapped equivalents
- Geography: US-based primary, EU operations welcome
Psychographics
- They have outgrown the "more content" mindset and want fewer, better assets
- Their sales team has lost trust in marketing's output and works around it
- They have tried at least one full-service agency and felt over-billed for under-thought work
- They want to be challenged by a partner who has seen the pattern before
- They believe content can move pipeline but cannot prove it yet
Trigger Signals
- "We are publishing more than ever and pipeline is flat."
- "Our sales team is not using anything marketing makes."
- "The CFO wants to know what content actually does."
- "We have keywords ranking and demos are not coming in."
- "Our agency hands us posts every week and none of it sounds like our buyer."
- "We just hired a head of demand gen and they are auditing everything."
Secondary ICP: The PE-Backed B2B Platform
PE-backed platforms are growing fast, scrutinized weekly, and live or die by pipeline efficiency. They came up under a different operating logic, and they need content that performs against a forecast, not a brand strategy.
They tend to be skeptical of agencies but starved for outside thinking. The combination is gold for us if we get in front of the right operator.
Firmographics
- Industry: Vertical SaaS, fintech infrastructure, healthtech, vertical marketplaces
- Revenue: $25M to $150M ARR, often post-acquisition
- Team size: Internal marketing of 2 to 6, recently hired or recently restructured
- Channels: Heavy on paid, weak on organic, often with a buried CRM and good intent data
Psychographics
- They are operating on quarterly OKRs and need pipeline movement, not brand work
- Their CMO is new (within 12 months) and looking for early wins
- They have seen agencies pitch them on "thought leadership" and rolled their eyes
- They will not buy anything without a forecast attached to it
Trigger Signals
- "We need to prove content can move our number this quarter."
- "We are spending on paid and the cost per opportunity keeps climbing."
- "Our investor wants to see pipeline diversification."
- "We have a sales team that is louder than our marketing team."
Who Is Not a Fit (Red Flags)
We say no to:
- Companies that want SEO content as a volume play
- Founders who insist on owning the editorial direction without sales input
- Companies that will not give access to sales calls or pipeline data
- Buyers shopping primarily on price ("what is your blog post rate?")
- Stage companies pre-product-market-fit looking for content to compensate
- Marketing leaders who view content as a writing service rather than a strategic function
Our Sweet Spot Clients Sound Like (Green Flags)
- "We have great product and a real story; the marketing is just not connecting."
- "Our sales team would tell you what we publish does not match what they hear on calls."
- "We need a partner that can actually sit with our reps."
- "We are tired of agencies that send us drafts we have to rewrite."
Target Buyer Personas
The VP of Marketing
Titles: VP Marketing, VP Demand, Head of Marketing
Pain: Caught between a CFO asking for ROI proof and a content team producing what feels right but cannot be measured. Has been burned by an agency before.
Win: "Northwood gave me a way to defend the content investment to the board with data nobody else had."
The Demand Gen Director
Titles: Director of Demand Generation, Director of Growth Marketing
Pain: Owns the pipeline number, depends on content for top of funnel, and cannot get the content team to align with the funnel they are running.
Win: "Finally I have content my SDRs send unprompted."
The CMO
Titles: CMO, Chief Marketing Officer
Pain: Trying to translate marketing activity into board-ready outcomes. Skeptical of agencies but understaffed internally.
Win: "Northwood thinks like an operator, not a vendor. They make my team sharper."
POSITIONING & OFFERS
Our Positioning: The Sales-Embedded Content Partner
Northwood does not produce content for the sake of an editorial calendar.
We embed with sales teams, learn what actually closes deals, and build content from real buyer conversations.
Most B2B content agencies start with a keyword tool. We start with a recording of last week's sales calls. That difference is not cosmetic. It changes what we recommend, what we produce, and how we measure success.
What Makes Us Valuable as Partners
- We Listen First, Always. Every engagement starts with sales call review. Not a survey. Not a workshop. Recordings, transcripts, lost-deal notes. We learn the buyer's actual language before we write a word.
- We Map Content to Deal Stages. Every piece of content has a job tied to a real moment in the pipeline. We do not produce orphan blog posts or thought leadership for its own sake.
- We Measure Influenced Pipeline. Pageviews are interesting. Influenced pipeline is the number that survives a CFO conversation. We instrument both and report on what matters.
- We Will Tell You to Stop. If a campaign is not moving pipeline, we say so. If your team is producing the wrong asset, we say so. We are not paid to make you feel good about your content investment. We are paid to make it work.
Core Offers
1. The Pipeline Diagnostic
Our entry point.
A four-week engagement that audits your current content engine against your pipeline data, sits in on your sales team's calls, and produces a roadmap for content that closes deals.
Includes
- Review of 12 to 20 recent sales calls (recordings and transcripts)
- Lost-deal postmortem analysis (last two quarters)
- Existing content audit against deal stages
- Buyer language extraction and theme mapping
- Content gap report tied to pipeline stages
- 90-day production recommendation with priorities and pacing
Output
- Pipeline Diagnostic report (40 to 60 pages)
- Live walkthrough with your marketing and sales leadership
- Implementation roadmap with budget guidance
Typical Fee: $35,000 fixed
Who it is for:
- B2B SaaS marketing leaders who have lost confidence in their content output
- Demand gen directors who need to defend content spend in the next board cycle
- New CMOs auditing their inherited marketing engine
2. Ongoing Content Engine
Cross-format content production grounded in the Pipeline Diagnostic.
We staff a strategist, an editor, and a research lead against your account. We sit on at least two sales calls per month. We produce, review, and measure content tied directly to your pipeline stages.
Includes
- Long-form content (case studies, deep guides, technical narratives)
- Short-form content (sales-enablement assets, email sequences, objection handlers)
- Quarterly content reviews tied to influenced pipeline data
- Monthly working sessions with your sales leadership
- Continuous buyer language extraction from new sales calls
Does NOT Include
- Paid media management
- SEO link building
- Pure brand creative or design system work
- Video production beyond editorial direction
Typical Fee: $18,000 to $32,000 per month, based on volume and stage coverage
Who it is for:
- Companies that have completed a Pipeline Diagnostic and are ready to operate against it
- Marketing teams that want a content partner who attends their sales meetings, not just their marketing standups
How We Talk About It
"Our entry point is the Pipeline Diagnostic because we will not write a word until we have heard your buyers."
"We do not sell content packages. We sell pipeline alignment, and content is how we deliver it."
"You can hire a cheaper content shop. You will not find a partner who can prove what their work moved."
DISCOVERY & QUALIFICATION
Discovery Is the First Diagnostic
We do not use discovery to "uncover pain points." We use it to find the gap between what a prospect's marketing team is producing and what their sales team actually needs.
That gap exists in almost every company we talk to. Our job is to find it precisely, name it back to the prospect in language they recognize, and let the relevance of the next step speak for itself.
Every discovery call should leave the prospect smarter about their own pipeline than when the call started.
The Discovery Call: Goals
- Understand the Pipeline Reality. What does the funnel actually look like, where are the leaks, what is the average deal size, who is buying.
- Map the Current Content Engine. What is being produced, by whom, against what brief, with what intended outcome.
- Surface the Sales-Marketing Gap. What does sales say about marketing's output. What does marketing think sales is missing. Who is right.
- Gauge Strategic Fit. Are they ready for a partner who will sit in their sales meetings. Will they share the calls. Will they tolerate honest findings.
Discovery Structure
- Open With Context (5 min)
- Set the tone: "We work very differently from most content agencies. We will probably ask about your pipeline before we ask about your content."
- Open question: "What made you take this call this week, specifically?"
- Pipeline Reality (10 to 15 min)
- "Walk me through your last three closed-won deals. How did they find you?"
- "What does your sales team say about the leads marketing sends them?"
- "If your CFO asked you to defend the content budget tomorrow, what would you point to?"
- Current Content Engine (10 to 15 min)
- "Who decides what your team produces each quarter?"
- "How does a piece of content get from idea to publish?"
- "When was the last time someone on your sales team forwarded one of your assets to a prospect?"
- Friction and Aspiration (10 min)
- "Where does the wheel come off in your current setup?"
- "If we were having this same conversation a year from now, what would have changed?"
- Close With a Finding (5 min)
- Reframe the gap: "From what you have described, it sounds like your team is producing top-of-funnel volume while your sales team is starving for objection-handling assets. Does that match what you see?"
- Propose the Diagnostic: "The most useful next step is probably a Pipeline Diagnostic. Here is what that looks like."
Strategic Questions We Like
- "Tell me about a recent deal that almost closed and did not. What did marketing produce that the sales rep used in that cycle?"
- "How does your team measure whether a piece of content was successful?"
- "If you could see a single dashboard about your content tomorrow, what would you want it to show?"
- "Whose buy-in do you need to make a decision like this, and what do they care about?"
- "What is the smallest version of this engagement that would feel like a win to you?"
Qualification Framework
Use this lightly. Do not weaponize it.
BANT-NW Diagnostic Lens
| Criteria | What to Look For |
| Budget | Annual content budget of $200K or above, or willingness to consolidate scattered spend |
| Authority | Decision-maker is on the call or actively involved within one step |
| Need | Stalled pipeline, declining content ROI, sales-marketing misalignment, or new leadership audit |
| Timeline | "We want this resolved this quarter" beats "sometime this year" |
| Sales Access | Willing to grant access to sales calls, lost-deal notes, and pipeline data |
| Strategic Fit | Values diagnosis over delivery and is willing to be challenged |
Red, Yellow, Green Light Filters
🟥 Red Light
- "We just need someone to write our blog posts."
- Will not provide access to sales calls or pipeline data
- Has decided the strategy already and wants execution
- Optimizing for cost per word
🟨 Yellow Light
- New marketing leader still learning the org
- Has been burned and is cautious but open
- Strong intent, slow procurement
🟩 Green Light
- "We know what is broken; we cannot tell you exactly why."
- Willing to put us on a sales call before signing anything
- Sales leader is in the room or invited to the next one
- Diagnostic value lands within the first 30 minutes
Qualification Checklist
Ask yourself these six yes/no questions after the call. If you are not at 5 of 6 or above, slow down before advancing.
| Question | Yes / No |
| Is there a real pipeline pain tied to content output? | ⬜ / ⬜ |
| Are they spending or willing to spend at our minimum engagement level? | ⬜ / ⬜ |
| Will they grant access to sales calls and pipeline data? | ⬜ / ⬜ |
| Is sales leadership willing to participate in the engagement? | ⬜ / ⬜ |
| Are they aligned with starting at a Diagnostic before any retainer? | ⬜ / ⬜ |
| Did they engage with the finding we surfaced on the call? | ⬜ / ⬜ |
Score:
- 6 of 6: Move forward today
- 5 of 6: Worth pursuing, address the friction
- 4 or below: Pause or reposition
Qualification Decision Tree
1. Is there a real pipeline-tied content problem?
→ No → Disqualify
→ Yes → Continue
2. Will they give us access to sales calls and pipeline data?
→ No → Reposition or disqualify
→ Yes → Continue
3. Is sales leadership willing to participate?
→ No → Flag delivery risk and reduce scope
→ Yes → Continue
4. Are they at our budget floor or willing to consolidate?
→ No → Disqualify or move to lighter engagement
→ Yes → Continue
5. Did the discovery finding land with conviction?
→ No → Schedule a second touch before proposing
→ Yes → Advance to Pipeline Diagnostic proposal
SALES STAGES & PIPELINE
Why This Matters
Pipeline hygiene is revenue visibility. We do not track leads. We track deal momentum, signal strength, and whether the next step is real or wishful.
Our process is short on stages and long on conviction. A deal moves only when there is evidence it should.
Sales Stage Definitions
| Stage | What It Means | Key Activities | Owner |
| 1. Identified | A real prospect from outbound, inbound, or referral | ICP check, light research, tailored outreach | Jamie / Max |
| 2. Discovery Booked | Prospect has confirmed a discovery call | Confirm attendees, request a recent sales call recording in advance | Jamie |
| 3. Discovery Complete | Discovery call held; finding surfaced; qualification scored | Update notes, run qualification checklist, decide go/no-go | Jamie |
| 4. Diagnostic Proposed | Prospect qualified; Pipeline Diagnostic scope and price presented | Send recap email, scope doc, NDA path to data access | Jamie |
| 5. Diagnostic Accepted | Engagement signed; deposit invoiced | Kickoff prep, assign delivery lead, confirm sales-call access | Jamie → Maya |
| 6. Retainer Proposed | Diagnostic complete; retainer scope and fee delivered | Tie scope to Diagnostic findings; align on KPIs | Jamie |
| 7. Retainer Accepted | Signed retainer; onboarding triggered | Setup call, access credentials, working rhythm defined | Maya |
| 8. Closed Lost | Deal exited at any stage | Log reason, tag pattern, schedule re-engagement if appropriate | Jamie |
| 9. Closed Won | Retainer or Diagnostic in delivery | Hand off to delivery, begin reporting rhythm | Delivery Team |
Pipeline Visibility: Red, Yellow, Green Tags
- 🟢 Green Light: Qualified, aligned, momentum present
- 🟡 Yellow Light: Friction in budget, timing, or access; movable but watch
- 🔴 Red Light: Misaligned or stalled; decide on rescue or release
Pipeline Tools
- HubSpot CRM as system of record
- Lead source field required at creation (inbound, outbound, referral, partner)
- Last touch date with weekly hygiene review
- Qualification score stored as a numeric field (0 to 6)
- ICP segment tag (Mid-Market SaaS or PE-Backed Platform)
Who Owns What
| Stage | Primary Owner | Support |
| Identified to Discovery | Jamie / Max | — |
| Discovery to Diagnostic Proposal | Jamie | Maya (delivery scoping) |
| Diagnostic Delivery | Maya | Editorial, Research |
| Retainer Proposal to Close | Jamie | Maya |
| Onboarding | Maya | Account Strategist |
Pipeline Review Rhythm
- Monday Pipeline Review (30 min): Jamie walks every active deal with Maya. Update statuses, kill stale opportunities, set the week's priorities.
- Friday Loose Ends (15 min): Quick scan of yellow-light deals. Decide on a touch or a release.
- Monthly Win-Loss Retro (60 min): Review last month's closed deals. What worked, what stalled, what to systematize.
SALES ASSETS & TOOLS
Why These Matter
Our sales assets are not collateral. They are evidence.
Every asset we send a prospect is meant to demonstrate, not describe, how we think. A prospect who receives a Northwood follow-up should not need to read the sentence "we are different." The asset itself should make that point.
Core Sales Assets
| Asset | Purpose | Format | Owner |
| Pipeline Diagnostic One-Pager | Plain-language explanation of what the Diagnostic is and what it produces | PDF | Jamie |
| Sample Diagnostic Report | A redacted Diagnostic from a past client | PDF | Jamie |
| Buyer Language Library | Anonymized examples of phrase-level extraction from real sales calls | Notion | Maya |
| Discovery Recap Template | Same-day follow-up with a finding, not a thank-you | Gmail template | Jamie |
| Case Study Library | Five short narrative case studies tagged by industry and pain | PDF and Notion | Jamie |
| Pricing Frame | One-pager that explains how we price and why | PDF | Jamie |
| Sales-Marketing Alignment Brief | Primer we send before discovery so marketing leaders bring sales leaders | PDF | Jamie |
Sales Ops Tools (Current Stack)
| Tool | Use | Notes |
| HubSpot CRM | System of record for deals and contacts | Required for all pipeline updates |
| Notion | Internal sales workspace, playbook, asset library | Source of truth for process |
| Gmail with templates | Outreach and follow-up | Templated for speed, customized for sender |
| Gong | Discovery and proposal call review | All calls recorded |
| Linear | Deal-specific tasks and follow-up tracking | Linked to HubSpot deal IDs |
In Progress and To Build
- Diagnostic ROI calculator (interactive, branded)
- Lost-deal postmortem template prospects can run themselves
- Sales call audit checklist for prospects to do before our discovery
- Industry-specific Diagnostic samples (fintech, healthtech, vertical SaaS)
- Objection-handler video library (60-second clips by topic)
Rules of Thumb for Using Sales Assets
- A finding beats a deck. Always.
- Never send a generic capabilities deck. If a prospect asks for one, treat it as a yellow-light signal.
- Customize every recap email. Same template, different finding, every time.
- If an asset does not move the deal, retire it.
OBJECTION HANDLING & COMPETITIVE POSITIONING
Our POV on Objections
Objections are not problems. They are the prospect telling you what they need to hear next.
A prospect who pushes back is engaged. A prospect who agrees with everything is rarely the one who buys.
We meet objections with specifics, not slogans.
Common Objections and How We Respond
"Why do you start with a Diagnostic? We already know what we need."
Response: You may. Most teams we talk to are right about the symptom and wrong about the cause. The Diagnostic is short and inexpensive relative to what you spend on content in a quarter. It either confirms your read or surfaces something you would have spent six months and a lot of money working around. If you are confident, we can scope a tighter version focused only on the area you want to test.
"Our internal team handles content. Why would we hire you?"
Response: If your internal team has the capacity to sit on twelve sales calls a quarter, build a buyer-language library from scratch, and tie every asset to a deal stage, you do not need us. Most internal teams we work with are excellent at execution and starved for outside pattern recognition. We are not here to replace your team. We are here to give them an unfair advantage and a thinking partner.
"Your price is higher than the agency we are talking to."
Response: Probably true. Most content agencies sell volume. We sell influenced pipeline. The price difference reflects the work, not the brand. Our typical client cuts content production by half and increases the pipeline contribution from content by two to three times in the first six months. If volume at the lowest cost is your goal, we are the wrong partner.
"Can you guarantee the Diagnostic will surface something useful?"
Response: We have run this engagement more than fifty times. Every one has surfaced at least one finding the client did not have before. We will not guarantee a specific outcome. We will guarantee that you will leave with information you did not have, presented in a way you can act on.
"What if we do the Diagnostic and decide not to continue?"
Response: Good. The Diagnostic is built to stand alone. The roadmap we deliver is yours. You can run it with your internal team, with another partner, or pause it. We win when the work works. If a retainer is not the right fit, we would rather you say so and refer us to the next person who needs a Diagnostic.
Competitive Positioning
When we are up against another firm, we do not trash them. We frame the choice.
| Competitor Type | What They Say | How We Respond |
| Volume content shops | "We will publish 40 pieces a quarter for a flat fee." | Volume is easy. Pipeline impact is the work. We start by figuring out which 4 of those 40 will actually move a deal. |
| SEO-led agencies | "We will rank you for high-intent keywords." | Ranking matters. Buyer language matters more. Our content gets sent inside sales conversations, not just clicked from search. |
| Boutique creative shops | "We do beautiful work that wins awards." | Beautiful work is great. Our work is sent by your sales team. Different scoreboard. |
| Internal team build-out | "Just hire two more writers." | If you can hire, train, and retain them inside twelve months, do that. We are the bridge that buys you the time and the system. |
| Big full-service agencies | "We do everything: paid, content, design, brand." | Doing everything means specializing in nothing. We do one thing and we do it inside your sales team's day. |
CLOSE PROCESS & HANDOFF
Closing Is Alignment, Not Pressure
We do not hard close.
If we have done discovery well, the close is mechanical. The prospect already knows the next step is the Diagnostic. Our job is to make it easy to say yes today.
The most common outcome is not "no." It is "I need procurement approval" or "let me confirm the budget." Our job is to make those conversations short and successful.
Close Triggers We Listen For
- "This is the conversation I have wanted to have for six months."
- "We have not heard this kind of analysis from anyone else we have talked to."
- "I need to bring my sales leader into this; they need to hear it."
- "What would the kickoff look like?"
When we hear these, we move directly to the Diagnostic next step.
How We Close
Step 1: Confirm the Finding
"Sounds like the gap you are seeing is between your content output and your sales team's actual pipeline. Fair summary?"
Step 2: Reaffirm the Path
"The cleanest way forward is the Pipeline Diagnostic. Four weeks, fixed scope, clear deliverable. It either confirms your read or surfaces what you have been working around."
Step 3: Frame the Engagement
"We will sit on twelve to twenty of your recent sales calls, audit your existing content against deal stages, and produce a roadmap. You get a 40 to 60 page report and a live walkthrough with your sales leadership."
Step 4: Lay Out the Next Step
"I will send a one-page recap and a scope document tonight. If you want to proceed, we can start with sales call access this week and have the kickoff scheduled inside seven days."
Step 5 (Optional): Hold the Slot
"Do you want me to hold a tentative kickoff slot two weeks out so we are ready when you are?"
Diagnostic Close Checklist
- ⬜ Recap email sent within 24 hours with one specific finding
- ⬜ Scope document delivered within 48 hours
- ⬜ Sales call access path confirmed (Gong, Chorus, or raw recordings)
- ⬜ Kickoff date proposed
- ⬜ Internal delivery team notified
- ⬜ HubSpot deal stage updated to Diagnostic Proposed
Diagnostic to Retainer Transition
When the Diagnostic completes:
1. Deliver the Findings (Live Walkthrough)
Cover:
- The pipeline-content gap we found
- The buyer-language patterns we extracted
- The specific assets that need to be killed, replaced, or redirected
- The 90-day production roadmap
2. Make the Recommendation
"If you want us to operate against this roadmap, here is what a retainer looks like. If you want to run it internally, the roadmap is yours and we can stay available for monthly reviews."
3. Propose the Retainer (Only When Aligned)
- Tie the scope directly to the roadmap
- Anchor the fee to the volume and stage coverage required
- Set the start date and the first 30-day milestone
4. Hand Off to Delivery
- Internal team aligned on goals, calendar, and access
- First sales call attendance scheduled inside seven days
- 30-60-90-day plan published in shared workspace
Retainer Onboarding Snapshot
| Step | Owner | Notes |
| Welcome and kickoff scheduling | Maya | Within three business days of close |
| Access checklist | Ops | Gong, HubSpot, content workspace, brand assets |
| Reporting cadence setup | Account Strategist | Monthly influenced-pipeline review |
| First 30-day priorities confirmed | Maya and Jamie | Drawn from the Diagnostic roadmap |
| Day-21 pulse check | Maya | Relationship health, scope adjustments |
SALES METRICS & PERFORMANCE TRACKING
Sales Is About Learning
We are not gaming a leaderboard. We are tracking signals so we can see what is working, what is stuck, and what to fix.
The point of the metrics is not to drive harder. It is to drive smarter.
Core Metrics We Track Monthly
| Metric | Description | Source |
| New Conversations Opened | Distinct prospects in real dialogue (not just touched) | HubSpot |
| Discovery Calls Held | Number of qualified discovery calls completed | HubSpot, Gong |
| Diagnostics Proposed | Count of qualified deals that received scope | HubSpot |
| Diagnostics Accepted | Count of paid Diagnostic engagements started | HubSpot, Invoicing |
| Diagnostic to Retainer Rate | Percentage of Diagnostics that convert to retainers | Manual |
| Win Rate (Qualified) | Closed-won versus closed-lost among qualified deals | HubSpot |
| Average Cycle Length | Days from first call to signed Diagnostic | HubSpot |
| Top Source of Won Deals | Inbound, outbound, referral, partner | Manual tag |
Optional view: Same metrics segmented by ICP (Mid-Market SaaS versus PE-Backed Platform) to see traction patterns.
Weekly Pipeline Rhythm
Monday Pipeline Review (30 min)
- Walk every active deal through stage and tag
- Identify stuck deals and assign a next action
- Flag hot leads requiring same-week follow-up
Friday Pulse (15 min)
- Did we open enough new conversations this week?
- Did any deal move forward?
- What is overdue for a touch?
Monthly Sales Retrospective
Review:
- Which deals closed and what the common pattern was
- Which deals stalled and where in the process
- What we learned about the ICP this month
- What asset, message, or sequence we should systematize next
Accountability Culture
We are not running a quota machine. We are running a system.
- Pipeline is momentum. If new conversations are not opening, the system is broken upstream.
- Follow-up is leverage. Most deals do not die. They drift. The drift is on us.
- Patterns beat anecdotes. One slow week is noise. Three slow weeks is a signal we need to fix.
CONTINUOUS IMPROVEMENT & TEAM COACHING
Sales Is a Skill System
We are not searching for a closer. We are building a process that strategic operators can step into.
That requires more than a playbook. It requires a coaching cadence and a willingness to revise.
What We Are Aiming For
- A sales motion that is consistent, diagnostic, and thoughtful
- A pipeline that is visible to the whole leadership team weekly
- A sales style that reflects our values: listening before pitching, evidence over conviction, candor over comfort
- A team that can sell, not a single seller carrying the load
Current Coaching Cadence
| Activity | Frequency | Owner |
| Discovery Call Reviews | Weekly | Jamie with the team |
| Pipeline and Deal Coaching | Weekly | Jamie |
| Asset and Message Refinement | Monthly | Jamie and Maya |
| Playbook Iteration | Quarterly | Jamie with team input |
These rhythms are required regardless of headcount or hiring plans.
What We Review in Sales Coaching
Call Structure and Flow
- Did the call surface a finding?
- Did the prospect leave smarter?
- Were we asking diagnostic questions or reactive ones?
Deal Motion and Follow-Up
- Did the next step land within 24 hours?
- Was the follow-up relevant or generic?
- Is the deal moving for a real reason?
Positioning and Confidence
- Are we anchoring on the Diagnostic as the entry point?
- Are we explaining our thinking or selling our service?
- Are we naming the gap or describing our process?
What Great Sales Looks Like at Northwood
- A specific finding beats a polished pitch
- Diagnostic discipline beats persuasive energy
- Calm conviction beats pressure
- Insight-led questions beat surface rapport
- "We will not work without sales access" beats "we can be flexible"
Building for the Future
As we grow, we will need:
- This playbook, kept current
- A trained-up Diagnostic delivery team
- A sales asset library that matches the playbook
- A coachable hiring profile and ramp plan
- A CRM workflow that reinforces the process
We do not need a sales unicorn. We need operators we can train into the system.
Final Thought: Progress Over Perfection
This playbook will change. That is the point.
What matters most is this:
We do not settle for what is working okay. We invest in what is working clearly.
THIS PLAYBOOK IS A SYSTEM, NOT A STATEMENT.
Run it.