BootcampCapstone · Deliverable 5

Pipeline Tracker & Honest Forecast

Builds on Topic 8.

What you'll produce

A CRM-style pipeline tracker for your Lumadesk accounts — every live deal with its stage, ARR, next step, close date, and an honest close probability — plus a weighted forecast and a working-backward activity plan that ties your quota to the exact number of meetings and outreach touches you need this quarter. This is the artifact that separates a rep who "stays busy" from one a sales manager trusts: it proves you can read a funnel, forecast without wishful thinking (Topic 4), and do the quota math that every SDR and AE lives by (Topic 8). In an interview, this single page is what lets you answer "walk me through your pipeline" and "how would you hit quota?" like someone who's already done the job — which is exactly the signal that gets entry-level reps hired.

Instructions

  1. List every live account in one table. Pull your named target (GearGrid) and your look-alike accounts from Deliverables 1–4. Give each row: Account · Stage · ARR · Next step (with a date) · Close date · Probability (%). Don't pad it — a real, honest pipeline of 6–8 named accounts beats a fake one of 30.
  2. Assign a stage from the standard pipeline. Use the Topic 4 stages: Prospecting → Discovery → Demo → Proposal → Negotiation → Closed-Won/Closed-Lost. Each account sits in exactly one stage based on where the deal actually is, not where you wish it were.
  3. Put a real ARR on each deal. Lumadesk runs ~$40/agent/month. Estimate each account's agent count, then agents × $40 × 12 = ARR. Show your math so the number is defensible (a 25-agent support team = $12,000 ARR). Keep deals inside the $18k–$60k band the territory is built for.
  4. Anchor probability to the stage, then adjust for evidence. Start from a stage baseline (e.g., Discovery ~20%, Demo ~40%, Proposal ~60%, Negotiation ~80%) and nudge up or down for real signals: a named economic buyer and a quantified pain raise it; a stalled deal or a "no budget this year" lowers it. Honesty is the graded skill — a pipeline of all-90% deals is a red flag, not a strength.
  5. Write the next step as a verb with a date. "Send recap + pricing by Thu 6/18," not "follow up." Every live deal must have one concrete, owned next action — deals die when nobody drives the next step (Topic 4).
  6. Compute the weighted forecast. For each open deal, ARR × probability = weighted value. Sum them. State your commit (deals you'd bet your job on, ~80%+), your best case (everything closes), and your weighted forecast (the honest middle). Name which one you'd tell your manager.
  7. Check pipeline coverage against your number. Total open pipeline ÷ your quarterly target = coverage ratio. You generally need ~3–4× coverage to reliably hit quota given drop-off (Topic 8). If you're under, say so and say what you'll do about it.
  8. Work backward from quota to activity. Start from your target, divide by average deal size to get deals needed, then walk up the funnel using your conversion rates (won→opps→demos→discoveries→meetings→outreach). End with a number you can act on Monday: "I need X new conversations a week."
  9. Write 3–4 sentences of honest commentary. Where is the pipeline thin? Which deal is most at risk and why? What's the one action that most changes the forecast? This is the "forecast like a professional" part — name reality, don't spin it.

Worked example

(You are the SDR/AE on the Lumadesk territory. Quarterly new-business target for this seat: $60,000 ARR. Average deal size in this territory: $15,000 ARR (~31 agents at $40/agent/mo). It's week 4 of a 13-week quarter.)

Pipeline tracker

#AccountStageARRNext step (owned, dated)Close dateProb.Weighted
1GearGrid (220-emp DTC outdoor gear)Negotiation$31,700 (66 agents × $40 × 12 = $31,680 ≈ $31.7k — org-wide seat count, not the 11 in discovery; see expansion note)Send redlined order form + 2-yr discount option by Thu 6/18; verbal yes from Devon Apraku (VP of Operations, economic buyer)6/3080%$25,360
2TrailPeak Apparel (DTC, 180 emp)Proposal$14,400 (30 agents)Walk economic buyer (CFO) through ROI one-pager on 6/19 call7/1560%$8,640
3Harborview Home Goods (e-com, 140 emp)Demo$12,000 (25 agents)Tailored demo on AI reply drafting booked 6/20; champion confirmed7/2240%$4,800
4Cedar & Co. (online services, 90 emp)Discovery$9,600 (20 agents)Discovery call 6/17; need to confirm budget + reach the VP7/3120%$1,920
5NovaCart (e-com marketplace, 260 emp)Discovery$21,600 (45 agents)Multi-thread: get intro to Support Director from my SDR contact by 6/238/1215%$3,240
6Brightline Supply (B2B2C, 110 emp)Prospecting$10,560 (22 agents)Touch 4 of sequence (LinkedIn voice note) 6/16; no reply yet8/2910%$1,056
7Summit Outfitters (DTC, 200 emp)Closed-Lost$16,800Chose incumbent (Zendesk renewal); re-engage Q4 when contract ends0%$0

GearGrid expansion note (how 11 agents became a 66-agent deal). Discovery (Deliverable 3) sized GearGrid's current support team at 11 agents (8 today + 3 they're hiring) and used 11 × $40 × 12 = $5,280 only as a cost-of-the-tool comparison to frame ROI against ~$65k/yr of wasted agent time — it was never the deal size. The actual order form covers the whole support org Lumadesk will run, not just the front-line email queue: Devon Apraku (VP of Operations) scoped it to all 66 seats that touch support tickets — the 11 front-line agents plus wholesale/VIP desk, returns/RMA, social and chat coverage, two team leads, and the shared seats QA and Ops use to audit replies. So the deal grew on purpose between discovery and negotiation as we multi-threaded past Maya Chen (the Head of Support champion from discovery) into the broader org — a normal land-the-team motion, not a number that drifted. One ARR carries forward identically from here: $31,700 (66 agents) in this tracker and in the Deliverable 6 portfolio. If you keep GearGrid at the 11-agent / $5,280 figure instead, that's also fine — but then it falls below this territory's $18k–$60k band, so swap it for a look-alike as your anchor deal and keep one number consistent across D3 → D5 → D6.

Open pipeline (rows 1–6): $99,860 ARR across 6 deals.

Forecast (three honest numbers)

  • Commit — $25,360. Only GearGrid clears my 80% confidence bar ($31,700 × 0.80): I have a verbal yes from Devon Apraku, the VP of Operations who owns the budget, a quantified "why now" (order volume doubled, three new hires, Trustpilot complaints about slow replies), and we're in redlines. This is the deal I'd bet my forecast on.
  • Weighted forecast — $45,016. Sum of ARR × probability across all six open deals. This is the number I'd give my manager: it bakes in honest drop-off rather than assuming everything closes.
  • Best case — $99,860. Everything open closes-won. Useful as a ceiling, dishonest as a forecast.

Against target: Commit ($25,360) covers 42% of the $60k quarterly goal; the weighted forecast ($45,016) covers 75%. I am still behind, and the honest read is that the gap now hinges on one of {TrailPeak, Harborview} converting on top of GearGrid — and on whether GearGrid actually signs at the full 66-seat scope rather than slipping back toward the 11-seat front-line-only deal in negotiation.

Pipeline coverage

Open pipeline $99,860 ÷ target $60,000 = 1.7× coverage. Healthy coverage is ~3–4× because most deals don't close. At 1.7× I am still thin — and the GearGrid expansion makes the coverage look healthier than it is, because a single deal now accounts for ~32% of open pipeline. The honest read: even at a great close rate, this pipeline likely misses quota, and it's concentrated, so a GearGrid slip hurts twice. The fix isn't to inflate probabilities; it's to add top-of-funnel now (see activity math below), because deals sourced this week won't close until next quarter, so the hole compounds if I wait.

Working backward: quota → activity

Using my own funnel conversion rates (from Deliverables 2–4 and territory benchmarks):

StepRateMathResult
Quarterly target$60,000 ARR
÷ avg deal size$15,00060,000 ÷ 15,0004 deals to close
÷ opp→won win rate25%4 ÷ 0.2516 qualified opps
÷ demo→opp rate60%16 ÷ 0.6027 demos
÷ discovery→demo rate50%27 ÷ 0.5054 discovery calls
÷ meeting-booked→held80%54 ÷ 0.8068 meetings booked
÷ outreach→meeting rate5%68 ÷ 0.05~1,360 outreach touches

Over a 13-week quarter that's ~5 discovery calls and ~105 outreach touches per week (≈21 touches/day across email, LinkedIn, and calls).

Reality check — compare what the funnel demands to what I actually hold, stage by stage:

StageFunnel demands (per quarter)I have nowGap
Qualified opps (Discovery+ and live)166 open deals (rows 1–6)−10
Demos271 booked/held (Harborview), 3 deals already past Demoshort by ~20+
Discovery calls542 in Discovery (Cedar & Co., NovaCart)−52
Deals to close41 at commit (GearGrid)−3

The diagnosis isn't "outreach is low" in the abstract — it's that every stage above Demo is starved. I'm carrying 6 open opps against a target of 16, and only 2 live discoveries against the 54 the math says I should run this quarter; even my held/booked demos (1, plus 3 deals already past Demo) sit far under the 27 the funnel demands. Because the gap is widest at the top (−52 discoveries, −10 opps) and the deals I do have are already maturing, no amount of working the existing 6 deals harder closes a 16-opp target. So the binding constraint is top-of-funnel volume feeding Discovery, not closing skill — and the leak compounds, since a discovery booked today won't reach Demo for weeks. My Monday action: book the GearGrid redline call, hold the 6/17 and 6/20 meetings, and add ~105 fresh touches a week to the four newest-fit look-alike accounts — enough, at a 5% reply-to-meeting rate, to put ~5 new discoveries on the calendar each week and start closing the −52 discovery / −10 opp gaps toward 3× coverage.

Honest commentary

The pipeline is front-loaded and concentrated: one strong deal (GearGrid, ~32% of open pipeline at $31.7k) carries the forecast, and behind it coverage is only 1.7×, so a single slip — TrailPeak's CFO going quiet, or GearGrid de-scoping from 66 seats back toward the 11-seat front-line team during redlines — drops me from "maybe makes quota" to "clearly misses." The stage-by-stage read makes the problem precise: I hold 6 open opps against a target of 16 and 2 live discoveries against 54, so the funnel is starved at the top, not jammed at the close. Most-at-risk deal: NovaCart — it's my second-biggest ARR ($21,600) but I have no champion and no economic buyer yet, so its 15% is generous; I'm keeping it honest rather than letting deal size tempt me into inflating it. The one action that moves the forecast most is volume, not finesse: because closes lag outreach by weeks, the ~105 touches/week I add now — sized to put ~5 new discoveries on the calendar weekly and chip at the −10 opp / −52 discovery gaps — are what protect next quarter; under quota pressure the wrong move would be to overpromise on this pipeline, while the right move is to qualify TrailPeak and Harborview hard, drive GearGrid to signature, and refill the top of the funnel today.

Rubric

The app's AI scores the learner's submission against these criteria and gives feedback. Levels: Needs work (1) / Solid (2) / Excellent (3). Passing = every criterion at Solid or above.

  • Pipeline tracker completeness & deal-size consistency — 1: missing stages, ARR, or next steps; placeholders left in; or the named target's ARR contradicts its discovery agent count with no explanation · 2: every live account has a stage, ARR, dated next step, and probability, and the named target's agent count/ARR matches what discovery (Deliverable 3) established · 3: ARR is shown with agent-count math, next steps are owned verbs with dates, a Closed-Lost/Won row shows real funnel discipline, and the same agent count and ARR for the named target carry identically into the Deliverable 6 portfolio — or, if the deal expanded since discovery, the tracker names the added seats/teams and the buyer who scoped them so the growth is a deliberate land-the-team motion, not a number that drifted.
  • Honest, stage-anchored probabilities — 1: arbitrary or uniformly high probabilities (everything 80–90%) · 2: probabilities track stage and are individually defensible · 3: probabilities start from stage baselines and are adjusted for real evidence (named buyer, quantified pain, stalls), with the riskiest deal explicitly kept honest rather than inflated.
  • Weighted forecast — 1: no forecast, or just summing all ARR as if every deal closes · 2: computes ARR × probability, sums it, and states commit vs. best case · 3: cleanly separates commit / weighted / best case, names which number goes to the manager, and states it against the quarterly target.
  • Pipeline coverage read — 1: not addressed · 2: computes coverage (pipeline ÷ target) and compares to a healthy ratio · 3: interprets the ratio honestly (e.g., "1.7× is still too thin vs. the 3–4× target"), connects thin coverage to drop-off and timing lag, flags concentration risk if one deal dominates pipeline, and names the fix.
  • Working-backward activity math — 1: missing or skips the funnel · 2: walks quota → deals → opps → meetings → outreach using stated conversion rates · 3: lands on a per-week, do-it-Monday activity number and reality-checks it stage by stage against current pipeline — stating the gap at each level (e.g., "have 2 discoveries, need 54; have 6 open opps, need 16") — so the named binding constraint follows from where the funnel is actually starved, not just from total pipeline dollars.
  • Honest forecasting & narrative — 1: spins or hides problems, or no commentary · 2: 3–4 sentences naming where the pipeline is thin and the most-at-risk deal · 3: forecasts like a professional — names reality under quota pressure, identifies the single highest-leverage action, and resists overpromising (echoing "stay honest under pressure").