Dialogue

Exercise 2 · Commercial acumen & growth strategy

$6M is reachable. Just not the way we are going after it.

Three things the brief does not say, and what each one changes. The target is not the problem. The route to it is. Every figure below is a stated assumption I would replace with an actual in week one.

$2.4M

The floor on the real gap, on the most flattering reading of the pipeline

90 days

Left to create anything that can still sign inside this year

83

Active partner sellers the $6M actually requires. 12 per manager

Anton Silaev · Manager, Partnerships Illustrative model · dialogue.co · Confidential 1 / 10

Dialogue

Stated first · the basis

Before a single number, here is what I am assuming.

Everything that follows is built on these nine, and every figure in the deck carries a chip back to the one it rests on. They are not all worth the same, so I have labelled each by where it came from. All eight get replaced with actuals in week one.

The published anchor $103.2M ARR 2,668,917 members so $38.67 of ARR per member per year, about $3.22 PEPM Dialogue Q4 2022 results (TSX: CARE), the last full public disclosure before the Sun Life acquisition in October 2023. Every dollar figure in this deck is built up from this one number.

A1

BenchmarkWe win about 1 deal in 3. Qualified B2B win rates run ~29%, and partner-sourced is the highest-converting motion there is

A2

DerivedA new client company is worth $60K a year: the $38.67 above, on a named-channel group of ~1,550 covered lives. Group size is the only part I am assuming

A3

BenchmarkDeals take about 6 months from creation to signature, gated by the 1 Jan and 1 Jul renewal calendar

A4

My estimate1 in 5 mapped accounts becomes a real opportunity. No industry benchmark exists for this

A5

My estimateAn active seller brings 4 opportunities a year. A dedicated seller would do 4 a quarter, but a benefits advisor is not a dedicated seller, and a one-off referral is not an active seller

A6

BenchmarkCommit closes 90% of the time, Best Case 40%. Best Case is usually quoted at 50 to 60%, so this is the conservative read

A7

From the brief"Beginning of Q2" means a calendar fiscal year, so it is April. Sun Life reports on a calendar year, so this should hold

A8

From the briefThe $6M counts ARR contracted this year. If it counts ARR live this year, plans starting 1 Jan or 1 Jul make the window shorter still

A9

From the briefThe $6M is gross new ARR. If it is net of churn, every dollar leaving the $79M base is added to the job: 5% attrition is $3.95M before I add anything

Two of the nine are pure estimates with nothing behind them, A4 and A5, and A5 is the one that moves the most. At 4 opportunities per seller a year I need 83 active sellers. At 16 I would need only 21. That single number is the difference between a resourcing problem and an activation problem, so it is the first thing I would measure in week one.

1 derived · 3 benchmarked · 2 estimated · 3 read off the briefWeek 1 replaces all nine with actuals2 / 10

Dialogue

Finding 1 · How big

$4M of pipeline is not $4M of revenue.

The brief says a $2M gap. That only holds if every dollar of the $4M closes. Depending on whether the $4M is Commit, Commit + Best Case, or all open pipeline, the real gap is between $2.4M and $4.8M. None of them is $2M, and it is answerable in hour one.

What actually closes this year Gap to the $6M target │ Target = $6.0M

A · the $4M is Commitdeals the team has committed to close

$3.6M closes $2.4M gap

B · the $4M is Commit + Best Casethe usual forecast number, split evenly

$2.6M $3.4M gap

C · the $4M is all open pipelineevery stage, nothing discounted

$1.2M $4.8M gap

$0Each reading applies that category's usual close rateA6 to the same $4M$6.0M

I plan against reading A. It is the most flattering of the three, so the $2.4M it produces is a floor on the gap, not an estimate. Every number in the rest of this deck is built on it.

Working gap: $2.4M, not $2MBigger again if the $6M turns out to be net of churn rather than grossA93 / 10

Dialogue

Finding 2 · The route

I can get to $6M. I cannot get there by selling more.

Three quarters to close, one quarter to create. Deals take about six months from creation to signatureA3 and the year ends 31 December, so an opportunity not created by the end of Q2 cannot sign in time to count. Q3 and Q4 are for closing what already exists. Which means if the answer is new business, this is the window it would have to fit into.

Still to close

$2.4M

After the $3.6M reading A already delivers

→

New pipeline needed

$8.0M

Because we win 1 deal in 3A1

→

New opportunities

133

At $60K per new client companyA2

→

Window to create them

90 days

Everything after 30 June signs next year

For scale: at $60K a groupA2, the entire standing pipeline of $4M is about 67 open opportunities, under ten per Partnership Manager. This asks for 133 more on top of it, created inside 90 days. Twice everything we have today, built from nothing, in a quarter that has already started.

So one route is closed. We would have to triple the pipeline in 90 days, and no amount of effort or pressure does that. But closed is not the same as impossible, it just means the $6M comes from somewhere else. Revenue already under contract and already in the funnel is wide open, and that is where the remaining $2.4M lives. This is a redirect, not a retreat, and it is what the next five slides are built on.

The target stays. The route changesTighter still if the $6M is measured on revenue live rather than contractedA84 / 10

Dialogue

Finding 3 · Where

An even split is the wrong split.

$6M across seven Partnership Managers is $857K each, 7.6% growth. That only holds if all seven books are the same size. With six named partners plus a long tail, they will not be, and the shape below changes what the one underperformer actually costs.

Book of business per Partnership Manager The long tail The underperformer, wherever they sit │ Portfolio = $79M

If the seven books were equal$11.3M each, $857K of quota each

$11.3M

What a named-partner portfolio usually looks likeIllustrative shape, not a claim about this team

$22M

$18M

$12M

$10M

$7M

$6M

$4M

$0Two managers carrying half the revenue is the normal shape, not the exception$79M

The first question is not how hard anyone is working. It is where the shortfall sits. Spread evenly across all seven, the problem is the way we sell, and pressure in Q4 will not fix a model. Concentrated in one or two, it is coaching and workload, and that one I can fix this year. The same underperforming manager at half attainment is a $150K hole on the smallest book and an $840K hole on the largest. That 5x range decides whether this is a coaching conversation or a restructuring one, and it is the single easiest thing to find out.

Attainment and book size, side by side, never attainment alone$6M ÷ 7 = $857K · half attainment on an average book = a $430K hole5 / 10

Dialogue

First 30 days

Measure first. The target comes second.

A number I invent before I have measured the baseline is a number I spend the rest of the year defending.

Week 1

The data

Every open deal by partner, type, stage, age and close date. Win rate and cycle time by partner type. Answers: is the $4M Commit, Best Case or all open pipeline?

Week 2

The people

1:1 with all seven Partnership Managers, the same six questions each so the answers compare. Answers: is the shortfall in one or two, or everywhere? Skill, will, or workload?

Week 3

The partner types

Split carriers, consultants, brokers and embedded, because each grows differently and at a different speed. Answers: where does this year's revenue actually come from?

Week 4

The plan

A range, the decisions I need from you, and the weekly routine that replaces end-of-quarter surprises. Lands: the VP review.

The six questions: what is in your book · your biggest untapped opportunity · which forecast deals you would bet your own money on · which partner salespeople sent us a deal this year, by name · what is blocking you · which partner you would hand over, and which you would take on.

The one thing I would do in week one regardless: find out which individual salespeople bring us deals. A partner is not a salesperson. An insurance carrier is a thousand salespeople, sometimes more, and maybe forty matter to us. If I cannot name the forty, every dollar of enablement is scattered rather than aimed. And every one of those names gets a call in the same fortnight: what is in your book right now that we could be part of? That is the fastest revenue in this plan and it costs nothing.

Measure, then set the target, never the other way roundSame six questions to all seven, so the answers compare6 / 10

Dialogue

The engine · working backwards

$6M is not the number. 83 active sellers is the number.

I do not plan from last year plus a growth percentage. I start at the target and work back to the activity that produces it, because activity is the only part of this chain I can manage on a Monday.

Target

$6.0M

Net new ARR this year

→

Deals

100

New groups of ~1,550 covered lives, so $60K eachA2

→

Qualified opps

333

Because we win 1 in 3A1

→

Mapped accounts

1,665

1 in 5 becomes realA4

→

Active sellers

83

4 opportunities each a yearA5. 12 per manager

The $60K is derived, not guessed. At the published $38.67 per member a yearA2, $6M is 155,000 new covered lives. Blended, a Dialogue organization is 53 members, but that average is the embedded tail: the new wins reported that same quarter were a large telecom, a public utility and a national hospitality group, so I am modelling the named-partner channel at ~1,550 lives a group. Halve the group and it is 200 deals and 167 sellers. Double it and it is 50 and 42.

The assumption this leans on hardest 4 opps per seller a year → 83 sellers, 12 per manager (modelled) 8 a year → 42 sellers, 6 each 16 a year → 21 sellers, 3 each 16 is the benchmark for a dedicated seller. A benefits advisor is not one, so I hold the conservative figure until week one gives me the real one. If it turns out to be higher, I need fewer sellers and the plan gets easier, which is the direction I would rather be wrong in. And 12 active sellers is roughly a third of what one Partnership Manager can carry, so this year's ceiling is activation, not capacity.

"Are we going to hit $6M?" is unanswerable in April. "Do we have 83 producing sellers and 1,665 mapped accounts?" is answerable today, and it is the same question. And when we come in short, this chain names which link broke.

Target → deals → opportunities → accounts → active sellersUnit economics from Dialogue's Q4 2022 public disclosure · $103.2M ARR, 2,668,917 members7 / 10

Dialogue

What I would do, in order

Ranked by how fast it pays, not by how much it is worth.

Something worth $2M that pays out in eighteen months does not help this year. In-year value counts only what can sign before 31 December, which is why lines 4 and 6 look smaller here than they are.

CarrierThousands of advisors and group specialists sit behind one agreement.Deepest pool of sellers

ConsultantFewer advisors, larger employers, high influence each.Most value per active seller

BrokerMany advisors, smaller groups, highest touch to activate.Widest pool, most volume

EmbeddedRevenue moves programmatically. No individual to recruit.Expansion, not activation

Sellers come from the first three. A single carrier has thousands of advisors on its own, so 83 across three types is a fraction of one percent of the pool: the constraint was never how many sellers exist, it is that nobody has named which of them matter. One activation philosophy, a different playbook per type, and each playbook answers two things before anyone is approached. Why does this seller want to sell Dialogue, whether that is commission, client retention or differentiation in their own renewal pitch. And what the route to that partner's advisors is. That answer sorts the book: partners who open their sellers are activation partners and they supply the 83. A partner that will not is a passive partner, handled like embedded, expansion rather than activation. Going around a carrier to its own people is how you lose the carrier.

#	Action	Cost	Time to revenue	In-year valueBar = the range, scaled 0 to $2.4M. Ticks every $0.6M	Confidence
1	Clean up the forecast	$0	Weeks 1–2	$0 of new revenue. Moves the reported number ±$0.5M by telling the truth	High
2	Surface deals already live in our partners' books	$0	Weeks 1–3	$0 – $0.5M. All of it upside. I will not commit to what I have not looked at yet	Medium
3	Sell more into clients we already have	Low	60–90 days	$0.8M – $1.8M · mid $1.3M	HighOnly if expansion counts as net new ARR
4	Get our partners' salespeople actually selling	Low	30–90 days, then ongoingFull ramp to 30–40 sellers per manager ≈ 12 months	$0.3M – $0.8M this year. The rest lands next year, by design	High
5	Redistribute at-risk accounts, including the underperformer's	$0	30 days	$0.3M – $0.6M. Recovers stalled pipeline, does not create new	Medium
6	Small bonuses and recognition for booking meetings	Small	60 days	$0.1M – $0.3M this year. Mostly builds next year's funnel	High
7	Sign up new partners	High	9–18 months	$0 in-year. Start it in Q2 anyway, and book it against next year	Cannot help

Two deliberate calls. Expansion is worth $1.3M and it hangs on one definition, which is why it is the first decision I need from you. And signing new partners is what an ambitious manager reaches for first, and it cannot pay this year. I would still start it in Q2, and say plainly that it belongs to next year rather than let it sit in this forecast looking like help.

$2.75M against a $2.4M gap if expansion counts. $1.45M if it does notMidpoints · I plan more than I need, because some of it slips8 / 10

Dialogue

The recommendation

$4.5M committed. Three decisions take it to $6.0M.

The full number is still on the table and it does not need more budget. It needs three answers from you, this quarter.

Committed, whatever you decide Unlocked by decision 1 Unlocked by decisions 2 and 3 │ Plan = $6.0M

Commit · $4.5MThe number I will be held to. $3.6M of Commit-stage pipeline, plus $0.9M I can start on Monday, held near the bottom of its range

$4.5M · 75% of plan

Likely · $5.3MWhat I actually expect to land once decision 1 goes my way. Adds expansion at the low end of its range

$4.5M +$0.8M

Plan · $6.0MThe number I was given. Needs expansion toward the top of its range, plus redistribution and activation finishing above their floor

+$0.7M

$0Each line includes the one above it. $6.0M asks for about half the $3.1M of upside sitting above the commit: demanding, not heroic$6.0M

Decision 1 · worth $1.3M, possibly far more

What exactly counts toward the $6M?

Two parts. Does expansion into the existing base count? Worth $1.3M, and without it $6M is unreachable even with every lever at maximum. Is the $6M gross, or net of churn? At 5% attrition on $79M that is $3.95M of gross new before I add a dollar. The definition is worth more than every lever on the last slide combined.

Decision 2 · worth $0.3M to $0.6M

Can I move accounts between managers in Q2?

Coverage should follow opportunity, and some of what is stalling is stalling because of who holds it. And if the 30-day checkpoint shows a will gap, I want backing to change the seat and move that spend to the other six.

Decision 3 · worth $0.3M to $0.8M

What comes off my managers to make room for 1:1 seller recruitment?

Sellers get recruited and enabled one at a time, by the manager who owns that partner. Not webinars. Twelve sellers each is about four hours a week, so I need to take something off them. Central enablement supplies the playbook for each partner type and the clinical backup. My managers do the recruiting.

What I am not doing: not telling you $6M is fine, not asking for headcount in my first month, and not counting new partner recruitment in this year's number. Weekly I report active sellers, accounts mapped and new pipeline created, so these three figures move as the evidence moves. A shortfall I can name in April costs far less than a forecast that breaks in October.

$4.5M committed · $5.3M with decision 1 · $6.0M with all threeThree answers, no budget9 / 10

Dialogue

Follow-up · three weeks later, projecting $4.5M

I committed to $4.5M. We are at $4.5M. The commit held.

In April I said $6M needed three decisions this quarter. None has been made, so the number is exactly where I said it would be. The forecast is working, and reporting $4.5M is not the same as accepting it.

1 · Where the $1.5M sits

It was never in commit. It sat behind the three decisions I asked for in April. A decision gap, not a performance gap. Of the pipeline that did move, three causes:

Late. Real deals, wrong year. Into next year's opening balance.
Lost. Reviewed one by one.
Never real. My forecasting error, not the team's, and I say so.

2 · What can still pay this year

The creation window is open until 30 June, but building from nothing now is thin. Four things actually move a May number:

Expansion into clients we already have.
Deals already live in our partners' books that we are not attached to yet.
Acceleration. Late-stage deals pulled forward.
Forecast hygiene. Tells the truth, adds nothing.

All short-cycle, all riding conversations that are already happening.

3 · What I need this week

The same three decisions from April, still open. Plus the one thing I would stop to fund them.

I would rather you turn something down in May than approve it in August, when the same yes is worth nothing.

I am reporting $4.5M and working to $5.3M. The report is what you can plan the business on. The difference between the two is what I am accountable for. That $0.8M comes from expansion, acceleration, and deals already moving inside our partners' books, not from pipeline built from scratch. The creation window shuts on 30 June, and anything started after it belongs to next year. Next year gets built from 83 active sellers upward, and that is what stops us having this conversation again next April.

Anton Silaev · Manager, Partnerships, final-round exerciseReport the honest number, refuse the miss, bring dated choices · dialogue.co · Confidential10 / 10