Joint working document · all figures in USD · prepared for joint working sessions · last updated 22 May 2026
Scenario logic. Worst / Realistic / Best stress three independent levers: cost cuts (Aspire org v2 + tech), business model conversion (% creator spend + % ad spend + annual contracts), and NRR improvement (Aspire CS playbook). Full breakdown in Scenarios tab. Cirqle NRR anchored to actual cohort data (M3 114.8% / M6 89.4%) in Cirqle cohorts tab.
Ernst Rustenhoven (CSO, The Cirqle) owns the end-to-end joint process: working sessions, business plan, financial model, due diligence, definitive agreements, and closing.
Working principals: Steven Lammertink and Anand Kishore on strategy, leadership, and commercial decisions. Leon co-leads the financial model with Ernst. Lars represents Aspire investor side.
Cadence: Ernst publishes a one-pager every Friday — decisions made · decisions deferred (with owner + date) · risks · next-week priorities. Status review every Wednesday 30 min.
| Topic | Position | Read |
|---|---|---|
| Signing target | Fri 29 May 2026 | End of joint working week. Term sheet expiration window already extended past 1 May per binding §13. |
| Closing target | Fri 24 Jul 2026 | ~2 months from signing. Exclusivity covers 60 days through 28 Jul. |
| Enterprise value | $40M combined ($33.3M Cirqle / $6.7M Aspire) | Reflects current standalone profiles; subject to net cash/debt adjustment at close |
| Equity split | 50% Cirqle · 10% Aspire · 40% pool | 5:1 implied ratio between Cirqle and Aspire enterprise value |
| Aspire cash at close | Min $4M unrestricted | Realistic from $5.8M reported. Confirm creator float exclusion |
| Leadership | Chair: Anand · CEO: Steven · President: Anand | Without-cause CEO/President termination needs unanimous Board |
| Board | 3 directors (1 each + independent within 180d) | Until independent seated, all decisions require unanimity |
| Exclusivity | 60 days from signing · standard NDA · non-solicit 12mo | Through 28 Jul if signed 29 May |
The Cirqle: AI-native performance-creator SaaS, EU base. $5.2M run-rate (May 26), trending to $13.6M EOY 2026 per FY26LE model. EBITDA margin scaling from 13% Jan to 39% Dec. Pricing: SaaS + % creator spend + % ad spend + 3% affiliate (future).
Aspire: larger, services + SaaS hybrid with established US enterprise base. $20M revenue, ~breakeven today (Q1 26 hires of +20 heads absorbing as cost, expected to drive future growth). NRR transition (47% → 60% steady-state target per Aspire deck). Creator liability of $14.4M to be managed as part of combined working capital plan.
Combined: US footprint via Aspire's installed base, joint CS strength, and revenue model expansion via % creator spend + % ad spend + annual contracts across both customer bases.
| Risk | Why it matters |
|---|---|
| $14.4M creator liability (Aspire) | Working capital item exceeds combined Day 1 cash. To be addressed in Session 5 financial model. |
| NRR transition (Aspire side) | Per Aspire deck: 47% Q1 26 with 60% steady-state target. Joint CS playbook to support the transition. |
| SAFE / convertible conversion mechanics | Per term sheet §4, all convertibles convert into Aspire equity before exchange. Mechanics need confirmation in DD. |
| Business model conversion friction | Aspire seat-based contracts to Cirqle % spend model: 10-15% churn risk if forced too fast. |
| Cap table and convertibles conversion | $7.8M of SAFE/CN convert into Aspire equity per existing terms before exchange — internal allocation needs to land cleanly. |
| Metric | The Cirqle | Aspire | Ratio |
|---|---|---|---|
| Revenue (current run-rate) | $3.7M | $10.8M SaaS | 1 : 2.9 |
| MRR (current) | $317k | $897k SaaS | 1 : 2.8 |
| Total revenue run-rate | $3.7M | $17.8M (incl. agency) | 1 : 4.8 |
| Forward ARR target Dec 2026 | $10M | $13M SaaS (base) | 1 : 1.3 |
| Forward total revenue 2026 | $10M | $20M | 1 : 2.0 |
| Metric | The Cirqle | Aspire | |
|---|---|---|---|
| 3-year revenue trajectory | tbd FY24/25 → $7.0M FY26 ($13.6M EOY run-rate) | $20.5M → $19.9M → $20.2M (flat) | |
| 3-year SaaS ARR trajectory | tbd FY24/25 → $13.6M EOY26 run-rate | $11.9M → $11.4M → $11.1M (-3%/yr) | |
| 3-year EBITDA trajectory | $1.4M FY25 → $2.1M FY26 ($5.3M EOY run-rate, 39% margin) | -$6.3M → -$3.2M → -$0.25M | |
| Current ARR growth | ~180% YoY | -3% SaaS / -8% total | |
| EBITDA margin (current) | 38% strong | ~breakeven today; -12% absorbing Q1 hires in transition |
| Metric | The Cirqle | Aspire | |
|---|---|---|---|
| NRR | Strong healthy | 47% Q1 26 in transition | |
| Projected steady state NRR | tbd in joint model | 60% (per Aspire deck) | |
| Renewal pool ($/quarter) | tbd in joint model | $3.9M Q1 26 |
| Metric | The Cirqle | Aspire | |
|---|---|---|---|
| Revenue per head (today) | $308k | $178k | 1 : 0.58 |
| Gross margin SaaS | tbd, likely 80%+ | ~70% (incl. delivery) | |
| Sales cycle | Mid-market AI-native pitch | Enterprise brand marketing | |
| Pricing model | SaaS + % creator spend + % ad spend + 3% affiliate (future) | Seat-based annual SaaS |
| Metric | The Cirqle | Aspire (orig) | Aspire (post-cleanup v2) |
|---|---|---|---|
| Total heads (today) | 12 | 100 | ~73 |
| Revenue/Sales | 2 | 7 | 7 (retained) |
| R&D / Engineering / Design | 7 | 17 | 12 |
| Customer Success | 1 | 18 | ~13-14 |
| Managed/Agency | 0 | 35 | 21 |
| Marketing | 0 | 8 | 8 (retained) |
| G&A / Exec | 2 (Steven + Ernst) | 15 | 12 |
| Total annual comp | tbd in joint model | $11.8M | $9.6M (-$2.2M cash + $0.4M benefits) |
| Dimension | The Cirqle | Aspire | |
|---|---|---|---|
| Revenue model | SaaS + % creator + % ad + 3% affiliate (future) | Seat-based SaaS + Managed Services | |
| Revenue mix | ~100% software | ~55% SaaS / ~40% Agency / ~5% other | |
| Buyer persona | Growth / performance marketing | Brand marketing / creator strategy | |
| Margin profile | ~80% gross / 38% EBITDA | ~70% gross / ~0% EBITDA today (-12% absorbing Q1 hires) | |
| AI integration | Native (built-in) | Non-existent |
| Item | The Cirqle | Aspire | |
|---|---|---|---|
| Cash | $450k | $5.8M Jan 26 | |
| Creator liability | None | -$14.4M Jan 26 working capital item | |
| Deferred revenue | tbd | ~$3M | |
| Net working capital | tbd | Negative, structural |
| Item | The Cirqle | Aspire | |
|---|---|---|---|
| Total capital raised | tbd in joint model | $30.0M (per cap table) | |
| Preference stack | tbd in joint model | $22.9M LP across A-1 / A / Seed | |
| SAFE/Convertibles | tbd | $7.8M with post-money mechanics |
| Dimension | The Cirqle | Aspire | |
|---|---|---|---|
| Geographic strength | EMEA (NL HQ) | US-only motion asset | |
| Brand recognition | Growing (incl. Enterprise) | Established US enterprise | |
| ICP/segment | Performance-led DTC + brand + enterprise | Brand-led DTC + enterprise | |
| Key partnerships | Meta, TikTok native | Shopify, Walmart, retail tech | |
| Defensibility | AI-native data flywheel | Installed base inertia |
| Risk | The Cirqle | Aspire | |
|---|---|---|---|
| Working capital | Likely clean low | -$14.4M creator liability to manage | |
| Regulatory | Standard SaaS | Money transmitter exposure elevated | |
| Customer concentration | unknown | likely top-heavy on agency | |
| Key person | Founder + CSO + Chief of Staff | CEO/CSO/VP layer recently hired | |
| Retention risk | Low (strong NRR) | High during transition (47% NRR) | |
| Cash runway | +EBITDA, low burn | $5.8M cash, -$3.6M EBITDA run-rate | |
| Total preference + SAFE | tbd in joint model | $30.7M across preference + SAFE |
Scenarios stress three independent levers: (1) cost cuts from Aspire org cleanup v2 and tech consolidation; (2) business model conversion (% creator spend + % ad spend + annual contracts) applied to Aspire's installed base; (3) NRR improvement on Aspire side from Cirqle playbook deployment. Each lever has independent worst / realistic / high settings — outputs below are joint outcomes, not lever ranges.
| Lever | Worst case | Realistic | Best case |
|---|---|---|---|
| L1. Further cost optimization (post-v2 baseline) | $0.5M Y1 / $1.5M Y2 — minimal tech consolidation | $1.0M Y1 / $3.5M Y2 — tech + early agentic Y2 | $2.0M Y1 / $6.5M Y2 — full tech consolidation + agentic Y2 |
| L2. Business model conversion + ACV expansion | 30% capture, $1M conv + $0.2M expansion Y1; $2.5M+$0.5M Y2 | 50% capture, $3M conv + $1.1M expansion Y1; $8M+$2.5M Y2 | 70% capture, $5.5M conv + $2.7M expansion Y1; $14M+$5M Y2 |
| L3. NRR improvement (Aspire) | Aspire NRR holds at 55%. $0.9M revenue lift on renewals | Aspire NRR climbs to 70% Y1 → 80% Y2. $2.5M / $3.6M lift | Aspire NRR climbs to 85% Y1 → 95% Y2. $4.2M / $5.3M lift |
| Cirqle NRR (per cohort data) | 95% (M6 89% sustained) | 105% (M3 strong + M6 moderation) | 112% (M1-M3 strong sustained) |
| Component | Worst Y1 | Real Y1 | Best Y1 | Worst Y2 | Real Y2 | Best Y2 |
|---|---|---|---|---|---|---|
| Cirqle organic | $9.0 | $10.0 | $11.0 | $11.0 | $14.0 | $18.0 |
| Aspire base (post NRR transition) | $15.0 | $18.0 | $19.5 | $13.0 | $17.0 | $19.0 |
| Model conversion (% creator + ad spend) | $1.0 | $3.0 | $5.5 | $2.5 | $8.0 | $14.0 |
| Cross-sell Cirqle modules to Aspire base | $0.5 | $1.5 | $2.5 | $1.5 | $4.0 | $7.0 |
| Expansion revenue (Aspire ACV uplift to Cirqle hybrid model) | $0.2 | $1.1 | $2.7 | $0.5 | $2.5 | $5.0 |
| Total revenue | $25.7 | $33.6 | $41.2 | $28.5 | $45.5 | $63.0 |
Day 1 baseline is post-v2 cleanup. The $2.66M Aspire org cleanup is already applied at Close. Day 1 combined cost is therefore $26.2M ($19.7M Aspire post-cleanup + $6.5M Cirqle), not pre-cleanup $30M. Further savings in Y1/Y2 come from tech consolidation, vendor renegotiation, and agentic agency transformation.
| Component | Worst Y1 | Real Y1 | Best Y1 | Worst Y2 | Real Y2 | Best Y2 |
|---|---|---|---|---|---|---|
| Day 1 combined cost base (post-v2) | $26.2 | $26.2 | $26.2 | $26.2 | $26.2 | $26.2 |
| Less: further tech & vendor savings (L1) | ($0.5) | ($1.0) | ($2.0) | ($1.0) | ($2.0) | ($4.0) |
| Less: agentic agency savings (Y2) | $0.0 | $0.0 | $0.0 | ($0.5) | ($1.5) | ($2.5) |
| Plus: retention bonuses (one-time + 24mo) | $0.8 | $0.8 | $0.8 | $0.4 | $0.4 | $0.4 |
| Plus: integration / migration cost | $1.0 | $1.0 | $0.5 | $0.6 | $0.3 | $0.0 |
| Plus: Cirqle reinvestment (growth headcount) | $0.5 | $1.0 | $1.5 | $1.0 | $2.0 | $3.0 |
| Total cost base | $28.0 | $28.0 | $27.0 | $26.7 | $25.4 | $23.1 |
| Y1 Worst | Y1 Real | Y1 Best | Y2 Worst | Y2 Real | Y2 Best | |
|---|---|---|---|---|---|---|
| Revenue | $25.7M | $33.6M | $41.2M | $28.5M | $45.5M | $63.0M |
| Cost | ($28.0M) | ($28.0M) | ($27.0M) | ($26.7M) | ($25.4M) | ($23.1M) |
| EBITDA | ($2.3M) | $5.6M | $14.2M | $1.8M | $20.1M | $39.9M |
| EBITDA margin | -9% | 17% | 34% | 6% | 44% | 63% |
| Implied EV at 5x EBITDA Y2 | — | — | — | $9M | $101M | $200M |
| Implied EV at 4x revenue Y2 (SaaS comp) | — | — | — | $114M | $182M | $252M |
Realistic case: $5.6M Y1 EBITDA / $20.1M Y2. This is the case the joint financial model in Session 5 should anchor on. Materially better than prior version because (a) Aspire is at breakeven today, not -$3.6M, and (b) ACV expansion on customer porting is now modeled separately.
Worst case: -$2.3M Y1 EBITDA, recovers to +$1.8M Y2. Happens if NRR improvement on Aspire stalls AND model conversion rejected. Mitigant: grandfather top 20 accounts, lock retention bonuses.
Best case: $39.9M Y2 EBITDA (63% margin). Requires aggressive model conversion (70% capture) AND Cirqle NRR sustains 112%. Cohort data shows M1-M3 sustains this but M6 drops to 89% — best case requires fixing the M3-M6 step-down before scaling.
| Aspire NRR 55% | Aspire NRR 70% | Aspire NRR 85% | Aspire NRR 95% | |
|---|---|---|---|---|
| Model conversion 30% capture | ($0.5M) | $3.5M | $7.5M | $10.0M |
| Model conversion 50% capture | $4.0M | $10.0M | $16.5M | $20.0M |
| Model conversion 70% capture | $11.0M | $20.0M | $28.0M | $34.0M |
Key insight: EBITDA outcomes are most sensitive to model conversion capture rate and the newly-modeled ACV expansion from porting. The strategic priority is the commercial conversation with Aspire's top 30 accounts: converting them to the Cirqle hybrid model captures both the % spend take rate AND the ACV uplift on the existing seat-based contract. Sensitivity table below uses prior baseline — to be refreshed in Session 5 against new revenue mix.
KPIs above reflect the realistic scenario from the Scenarios tab. Worst and high cases bracket this view. The Combined P&L walk further below builds the line items underneath these numbers for the realistic case.
| Function | Cirqle | Aspire (orig) | Combined Day 1 (v2) | Combined M24 |
|---|---|---|---|---|
| CEO / Executive | 2 (Steven + Ernst) | 2 (Anand, COO) | 4 (Steven CEO, Anand President, Ernst, COO) | 4 |
| Revenue / Sales | 2 | 7 | 9 (Aspire 7 + Cirqle 2) | ~14 |
| Marketing | 0 | 8 | ~8 | ~11 |
| Customer Success | 1 | 18 | ~14-15 (VP CS retained) | ~16 |
| Managed / Agency Services | 0 | 35 | 21 | ~14 (agentic by then) |
| R&D / Engineering / Design | 7 (6 eng + 1 design) | 17 | 19 | ~17 |
| G&A (Finance, People, BizOps) | 0 | 13 | ~10 | ~10 |
| Total (today) | 12 | 100 | ~73 (Aspire) + 12 (Cirqle) = 85 | ~85 |
Source: Aspire's 2Org_Chart_as_of_05192026_v2 reflects a concrete cleanup plan with adjusted comp by line. Net effect: ~27 heads cut, $2.66M annualized savings ($2.22M salary + $0.44M benefits/taxes).
| Department | From | To | Cut | Comp savings | Decision |
|---|---|---|---|---|---|
| Managed / Agency Services | 35 heads / $2.95M | 21 heads / $2.05M | -14 heads | $894k | 14 of 28 Campaign Associates and Managers exit — prep for agentic agency |
| R&D | 17 heads / $2.24M | 12 heads / $1.68M | -5 heads | $557k | Eliminate 2 SWE, 2 Sr PM, 1 PM — duplicated by Cirqle product team |
| Customer Success | 18 heads / $1.69M | ~13-14 heads / $1.27M | -4 to -5 heads | $423k | Quarter cut across CS layer (4-5 roles below VP), VP CS retained at full comp |
| G&A People Operations | 4 heads / $445k | 3 heads / $240k | -1 head | $205k | Sr. Director People Ops eliminated |
| G&A Finance & Accounting | 8 heads / $671k | 6 heads / $536k | -2 heads | $136k | Deal Desk Lead + Specialist eliminated — Cirqle owns the new pricing model |
| Revenue / Sales | 7 heads / $2.02M | 7 heads / $2.02M | 0 | $0 | Fully retained — Strategic Sales Director + 6 reps |
| Marketing | 8 heads / $1.03M | 8 heads / $1.03M | 0 | $0 | Fully retained — US brand muscle |
| G&A Executive + BizOps | 3 heads / $785k | 3 heads / $785k | 0 | $0 | Retained Day 1 (Anand as President + COO) |
| Aspire total | 100 / $11.83M | ~73 / $9.61M | -27 heads | $2.22M | Plus $0.44M benefits/taxes = $2.66M annualized |
| Synergy | Y1 ($M) | Y2 ($M) | Logic |
|---|---|---|---|
| R1. % of creator spend | $2.0 | $5.0 | Aspire customers run $100M+ creator spend unmonetized. Convert top 30 to 2-3% take. |
| R2. % of ad spend | $1.0 | $3.0 | Partnership ads attribution layer on Aspire's enterprise base. |
| R3. Annual contract conversion | $0.8 | $1.5 | Aspire monthly/quarterly contracts to annual prepaid. Cashflow + retention. |
| R4. NRR uplift via Cirqle playbook | $2.0 | $5.0 | 47% → 75% NRR pulls $2-5M of lost revenue back. |
| R5. Cross-sell Cirqle modules | $1.0 | $3.0 | Performance attribution, AI campaign tooling into Aspire enterprise. |
| R6. Win-back churned | $0.3 | $0.7 | Aspire alumni list re-engaged with combined offer. |
| Revenue subtotal | $7.1 | $18.2 | |
| C1. Day 1 OpEx cuts (org v2) | $2.5 | $2.7 | $2.66M annualized run-rate from Day ~75 = ~$2.5M Y1 (timing). Full Y2. |
| C2. Tech / vendor consolidation | $0.4 | $0.6 | Duplicate SaaS, infra, observability. Cirqle stack wins. |
| C3. Agentic agency (downstream) | $0.4 | $2.5 | Y2: remaining Campaign team to ~14 from 21 via AI. Y1 prep only. |
| C4. Office / facilities | $0.0 | $0.1 | Minor. Both already remote-first. |
| Cost subtotal | $3.3 | $7.9 | |
| Gross synergy | $10.4 | $26.1 | |
| Less: one-time costs (severance, integration) | ($1.5) | ($0.2) | $185k severance + $1M integration / change mgmt |
| Less: risk adjustment (50% Y1, 25% Y2) | ($5.2) | ($6.5) | Probability-weighted |
| Net synergy | $3.6 | $19.4 |
| Line | 2026 Y0 (combined) | 2027 Y1 | 2028 Y2 |
|---|---|---|---|
| Cirqle SaaS / subscription (incl. % spend, affiliate future) | $10.0M | $10.0M | $14.0M |
| Aspire base revenue (post-NRR transition) | $20.0M | $18.0M | $17.0M |
| Model conversion (% creator + ad spend) | $0.0M | $3.0M | $8.0M |
| Expansion revenue (ACV uplift on porting) | $0.0M | $1.1M | $2.5M |
| Cross-sell Cirqle modules to Aspire | $0.0M | $1.5M | $4.0M |
| Total revenue | $30.0M | $33.6M | $45.5M |
| Cost base (Day 1 post-v2 = $26.2M) | ($26.2M) | ($28.0M) | ($25.4M) |
| EBITDA | $3.8M (13%) | $5.6M (17%) | $20.1M (44%) |
Y0 (~$0M EBITDA) is the Day 1 combined baseline if nothing changes — Cirqle's $3.5M EBITDA offsets Aspire's $3.6M loss. Y1 ($4M / 12% margin) driven by Day 1 cost cuts ($2.5M) plus early model conversion ($3M) and first cross-sell wins. Integration costs and retention bonuses absorb ~$2M of that. Y2 ($16.5M / 38% margin) driven by model conversion compounding ($8M run-rate), NRR improvement on Aspire (70%→80%), and agentic agency cost reduction. The mix shifts from 100% Cirqle SaaS + Aspire base in Y0 to 30% model conversion + cross-sell in Y2, reframing the entity as a hybrid SaaS + performance platform.
Other scenarios: worst case Y2 $1.8M EBITDA, best case Y2 $39.9M. Full breakdown in Scenarios tab.
| Risk | Impact | Mitigant |
|---|---|---|
| Customer churn during migration | 15-20% gross logo churn in migrated cohorts could cost $2-3M ARR Year 1 | Sequence migration carefully, retain Aspire CS team, contract incentives for early movers, dedicated migration PMs |
| Revenue model conversion resistance | Aspire customers signed seat-based contracts. Forcing transaction-based pricing + annual upfront could trigger 10-15% churn or partial price erosion if discounting required to retain | Grandfather top 20 accounts on existing terms Year 1. Offer hybrid pricing (lower seat fee + transaction take). New contracts default to Cirqle architecture. Avg revenue lift target +30%, not +50%, to manage friction |
| VP CS retention (key person) | VP CS is critical to Aspire customer continuity through the transition | Full comp retained + 24mo retention bonus vesting. Reports to CEO. Document playbook in Month 1 |
| Anand/Steven friction at the top | President vs CEO scope ambiguity. Without-cause termination needs unanimous board, which means deadlock risk if relationship sours | Document scope clearly in employment agreements pre-close. Independent board director seated within 90 days, not 180. RACI on all major decisions. |
| Aspire internal allocation | Per term sheet §9, internal waterfall is Aspire's responsibility. Mechanics need to land cleanly to retain Anand and key Aspire employees. | Discuss in Session 3 (Org). Consider NewCo grants from the 40% pool for key Aspire leaders alongside HoldCo allocation. |
| Creator liability working capital | $14.4M creator float to be managed alongside combined Day 1 cash position | Joint working capital plan in Session 5. Discuss creator payment terms standardization. Consider $3M revolver post-close. |
Scope. Jointly produce a Business Plan and a Financial Model for the combined entity.
Posture. Neutral, not due diligence. Both companies described from a single perspective, strengths and weaknesses on each side addressed symmetrically.
Format. One session per topic, each 1–1.5h. Output per session captured in a single living document: decisions made · decisions deferred (owner + date) · risks.
Cadence. All five sessions covered in the week of Monday 25 May 2026. Timeline: ~2 months end-to-end through to Close.
| Day | Date | Session | Time | Process owner | Participants |
|---|---|---|---|---|---|
| Mon | 25 May | S1 Product strategy, platform & tech integration | 1.5h | Ernst (owner) | Steven, Anand, both CTOs |
| Tue | 26 May | S2 Commercial offering, pricing & margin | 1.5h | Ernst (owner) | Steven, Anand, VPs Sales/CS, Leon |
| Wed | 27 May | S3 Leadership orgchart | 1h | Ernst (owner) | Steven, Anand, Leon |
| Thu | 28 May | S4 PMI tracks, goals, timeline, KPIs | 1h | Ernst (owner) | Steven, Anand, both PMOs |
| Fri | 29 May | S5 Joint Financial Model build + term sheet sign | 3h working session | Ernst (owner) | Leon, Steven, Anand (decisions + signature) |
Cadence ground rules. Each session starts on time and ends with a written one-pager owned by Ernst: decisions made · decisions deferred (owner + date) · open risks. Pre-reads circulated 24h ahead. Friday session is a working session — Leon and Ernst arrive with standalone baselines already aligned on methodology, with term sheet signature at session close.
Outcome: Agreed product portfolio for the combined entity, build / migrate / consolidate decisions, and target tech platform.
| Topic | Owner |
|---|---|
| Products each company brings today — enabled by their respective tech platforms | Both CTOs |
| What the best product in the market looks like — target state | Steven + Anand |
| Product portfolio for the combined entity — which products the platform must offer | Steven + Anand |
| Per product: do we have it — migrate, consolidate, or build from scratch | Both CTOs |
| Investment priorities by product and capability | Both CTOs + Steven |
| Target tech platform, migration architecture and sunset approach | Both CTOs |
| Joint AI roadmap and security / data / compliance baseline | Both CTOs |
| ✓ | Item | Done when |
|---|---|---|
| Product catalog mapped per side (capability × product matrix) | Single matrix in shared doc with both sides' products on the same axes | |
| Target product portfolio defined (5-8 product lines max) | Named, scoped, with primary ICP per product line | |
| Build / migrate / consolidate decision per product | Decision logged with owner and Day 1 / 90 / 180 / 365 milestone | |
| Target tech platform named (Cirqle stack, Aspire stack, or hybrid) | Single answer with sunset timeline for the other | |
| Migration architecture sketched (data, identity, integrations) | One-page architecture diagram | |
| AI roadmap agreed (where Cirqle AI native applies, where Aspire AI bolt-ons sunset) | 12-month roadmap with quarterly milestones | |
| Security/data/compliance baseline (SOC 2, GDPR, US state privacy) | Gap list per side with remediation owners | |
| M3-M6 NRR step-down on Cirqle cohorts — product root cause hypothesis | Working hypothesis with diagnostic in Session 2 |
Outcome: Agreed commercial offering per product (pricing, revenue and margin model) plus GTM motion and customer migration plan.
| Topic | Owner |
|---|---|
| Current customer base, segmentation and ICP — both sides | VPs Sales/CS |
| Per product: pricing, revenue model and margin model | Steven + Anand |
| Packaging and bundling direction for the combined offer | Steven + Anand |
| GTM motion per region (EU / US) and per segment | VPs Sales |
| Customer migration plan: scope, sequencing, take-rate target | VP CS Aspire |
| Revenue and cost synergies — identification and phasing | Leon + Ernst |
| Retention programme and cross-sell paths | VP CS Aspire + Cirqle CS |
| ✓ | Item | Done when |
|---|---|---|
| ICP definitions per product line (segment × use case × buyer) | One ICP statement per product line, signed off by both CEOs | |
| Pricing architecture: % creator spend + % ad spend + annual contract terms | Tiered pricing table with target ACV per tier | |
| Margin model per product (gross margin assumption, cost of delivery) | Per-product margin in joint model template | |
| Customer migration sequencing (top 20 enterprise grandfathered, next 50 transitioned, long tail standardized) | Tagged customer list with migration wave and date | |
| Take rate targets by tier (e.g. 2% creator spend / 1.5% ad spend / annual lift) | Locked numbers for joint model | |
| NRR target by region and segment (anchored to Cirqle cohort baseline + Aspire transition target) | Scenario settings: 70% Y1 / 80% Y2 realistic per scenarios tab | |
| Cross-sell paths Cirqle modules → Aspire enterprise base (top 25 named) | 25 named accounts with module fit assessment | |
| Win-back motion for churned Aspire customers | Target list, offer construct, contact owner |
Outcome: Agreed leadership orgchart and role mapping, building on the org cleanup v2 work, with a consistency check against Sessions 1 & 2.
| Topic | Owner |
|---|---|
| Build on prior work: broader org chart (org cleanup v2 is starting point on Aspire side) | Anand + Steven |
| Leadership orgchart — who leads and who runs what | Steven + Anand |
| Role mapping for senior leadership; retentions and severances | Steven + Anand + Ernst |
| Equity-plan harmonisation for leadership (SARs / options / ESOP) | Steven + Ernst + Leon |
| Retention packages for key individuals | Steven + Anand |
| Consistency check: does the leadership team support the product, platform and commercial decisions from Sessions 1 & 2 | Steven + Anand |
| ✓ | Item | Done when |
|---|---|---|
| C-suite mapped: CEO, President, CFO, CTO/CPO, CRO, CMO, VP CS, VP People | Named individuals or "open" with hiring spec by Day 30 | |
| Reporting lines locked through VP layer | Single org chart, ~12 boxes deep | |
| Aspire org cleanup v2 confirmed: 27 heads exit, $2.66M savings, 30-day severance | Each named role decision logged | |
| VP CS retained at full $330k comp + 24-month retention bonus | Bonus structure documented | |
| Strategic Sales Director retention package (lock the relationships) | Bonus structure documented | |
| Anand transition to President — scope, RACI vs CEO, communication plan | Written scope document, both signatures | |
| Equity plan harmonisation (Cirqle ESOP vs Aspire SAR/option) post-close | Conversion ratio and 40% NewCo pool allocation logic | |
| Top 10 retention targets identified with package sizing | Named list, total retention cost ~$800k | |
| WARN Act and EU labor law timing reviewed for all exits | Date-stamped notice plan, legal sign-off |
Outcome: Agreed PMI structure: workstreams, owners, milestones and KPI tree.
| Topic | Owner |
|---|---|
| PMI workstreams and owners | Steven + Anand |
| Milestones and integration timeline | Both PMOs |
| KPI tree for the combined entity | Leon + Ernst |
| Internal and external communications plan | Marketing leads + CEOs |
| ✓ | Item | Done when |
|---|---|---|
| PMI workstreams defined (Product, GTM, CS, Finance, People, Legal, Tech) | 7-9 workstreams with named owners on each side | |
| Integration milestones at Day 1, 30, 60, 90, 180, 365 | Milestone gantt with hard dates | |
| KPI tree: 5 top-line KPIs (revenue, NRR, EBITDA, headcount, customers) cascade to 20 leading indicators | Tree document, dashboard skeleton | |
| Weekly cadence: PMI steerco, workstream standups, all-hands | Calendar invites sent | |
| Communications plan: customer comms, employee comms, market comms (Day -1, Day 0, Day 7) | Drafted scripts and FAQs for each audience | |
| Risk register with mitigants and owners | Top 20 risks logged, each with owner and review cadence | |
| Decision rights map (RACI) for PMI period | Single RACI document signed off by both CEOs |
Outcome: A single, jointly-owned model translating Sessions 1–4 into numbers. Process owner: Ernst (Cirqle CSO). Co-lead on model build: Leon (Aspire).
| Topic | Owner |
|---|---|
| Standalone baselines — aligned definitions and methodology | Leon + Ernst |
| Revenue build by segment and region (FY26–28) | Leon + Ernst |
| Cost base, headcount, integration and retention costs (org cleanup v2 = the cost input) | Leon + Ernst |
| Synergy schedule and migration take-rate scenarios | Leon + Ernst |
| Capital structure, prefs, SAFE/CN, waterfall and dilution | Leon + Ernst + counsel |
| Three-statement output, scenarios and sensitivities | Leon + Ernst |
| ✓ | Item | Done when |
|---|---|---|
| Aligned chart of accounts (revenue, COGS, OpEx categories) | Single COA both sides map to before session | |
| Standalone P&L per company FY23-FY25 + FY26 forecast | Two clean tabs in joint model | |
| Combined revenue build by product, segment, region (FY26-28) | Build tab feeding the consolidation | |
| Cost build by department per scenario (org cleanup v2 + retention + integration) | Cost tab with toggleable scenario switch | |
| NRR module: Cirqle cohort-based + Aspire transition curve | NRR tab driving the renewal revenue line | |
| Synergy schedule with phasing (Y1 partial / Y2 full) | Synergy tab linked to scenario switch | |
| Three scenarios (worst / realistic / high) per Scenarios tab | Toggle delivers the three EBITDA outcomes consistent with this portal | |
| Three-statement output: P&L, balance sheet, cash flow | BS includes creator liability run-off, deferred revenue, working capital | |
| Cap table waterfall: prefs, SAFEs, conversion, NewCo dilution | Cap table tab with output to fully-diluted ownership | |
| Sensitivities: NRR × take rate × cost cut | 2-axis sensitivity table on Y2 EBITDA |
| Item | Owner | Deadline |
|---|---|---|
| Cirqle FY23/24/25 P&L shared with Leon under NDA | Ernst | Fri 22 May |
| Aspire customer list with ACV, tenure, NRR by cohort shared with Ernst under NDA | Leon | Fri 22 May |
| Aligned chart of accounts template | Leon + Ernst | Fri 22 May |
| Both product catalogs with capability maps for Session 1 | Both CTOs | Sun 24 May |
| Org cleanup v2 walked through with Anand pre-Session 3 | Anand | Tue 26 May |
| Cirqle cohort data (per Cohorts tab) shared with Leon | Ernst | Fri 22 May |
| This portal shared with Anand + Leon as joint working baseline | Ernst | Fri 22 May |
Note on pace. Five sessions in five days is tight. The trade-off is momentum vs depth — momentum wins here, because every week without alignment is a week of competing operating decisions on both sides. Anything that can't be closed in the session is logged as a deferred decision with owner and date, not held up.
Reference data for the joint working sessions. Click any section to expand.
Source. Cirqle internal cohort analysis · Post-trial (≥3mo) · NRR view · snapshot 22 May 2026.
Headline. Cirqle blended NRR profile: 112.7% at M1 → 114.8% at M3 → 89.4% at M6. The expansion in the first quarter post-trial is strong; the M3-to-M6 step-down is the area requiring product/CS attention.
Why this matters for the combined entity. Cirqle's playbook delivers strong early expansion. Applied to Aspire's base (currently at 47% NRR), the realistic ceiling is the Cirqle blended profile, not the M3 peak. Joint model in Session 5 should anchor Aspire NRR targets at 70% Y1 / 80% Y2, not at Cirqle's M3 peak of 115%.
| Cohort | Size | Initial (€) | M0 | M1 | M2 | M3 | M4 | M5 | M6 | M7 | M8 | M9 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 2026-04 | 14 | €30.2k | 100.0% | — | — | — | — | — | — | — | — | — |
| 2026-03 | 14 | €30.9k | 100.0% | 112.7% | — | — | — | — | — | — | — | — |
| 2026-02 | 14 | €24.1k | 100.0% | 99.6% | 76.6% | — | — | — | — | — | — | — |
| 2026-01 | 9 | €20.0k | 100.0% | 107.3% | 74.2% | 103.3% | — | — | — | — | — | — |
| 2025-12 | 3 | €8.3k | 100.0% | 87.6% | 67.1% | 48.8% | 0.3% | — | — | — | — | — |
| 2025-11 | 6 | €8.9k | 100.0% | 130.2% | 121.0% | 131.8% | 105.6% | 94.4% | — | — | — | — |
| 2025-10 | 1 | €6.0k | 100.0% | 72.0% | 79.4% | 78.9% | 0.0% | 0.0% | 0.0% | — | — | — |
| 2025-09 | 4 | €18.8k | 100.0% | 98.3% | 152.0% | 101.8% | 156.8% | 167.6% | 101.8% | 99.9% | — | — |
| 2025-08 | 5 | €20.0k | 100.0% | 126.2% | 98.3% | 137.6% | 97.2% | 77.3% | 80.2% | 70.3% | 71.0% | — |
| 2025-07 | 5 | €8.3k | 100.0% | 167.8% | 117.8% | 202.4% | 156.9% | 129.0% | 126.3% | 116.7% | 89.0% | 115.0% |
| Period | Blended NRR | Read |
|---|---|---|
| M1 (first month post-trial) | 112.7% | Strong onboarding-driven expansion. Customers expanding spend in first billing month. |
| M3 (end of first quarter) | 114.8% | Sustained expansion. Quarterly-billing smoothing visible. Peak retention point. |
| M6 (six months in) | 89.4% | Step-down. Some cohorts hold 100%+ (2025-09, 2025-07); some collapse (2025-12). Variance driven by ICP fit at acquisition. |
| M12+ | tbd | Insufficient cohort depth at this snapshot. By Session 5 (joint model), pull M12 NRR for 2024 cohorts to set the long-tail floor. |
| Scenario | Cirqle NRR assumption | Aspire NRR target | Logic |
|---|---|---|---|
| Worst | 95% | 55% | Assumes M6 89.4% sustained, no playbook improvement on Aspire side |
| Realistic | 105% | 70% Y1 / 80% Y2 | Cirqle M3 peak moderates by M6; Aspire benefits from playbook deployment |
| Best | 112% | 85% Y1 / 95% Y2 | M1-M3 strong sustained through M6 via ICP filter; Aspire converges to Cirqle profile |
Strategic read: Cirqle's M3 NRR is best-in-class. The M3-M6 step-down is the highest-leverage internal improvement available. Closing that gap before bringing on Aspire customers is the right sequencing, because Aspire will accelerate revenue but stress the same point in the customer lifecycle. Session 1 (Product) should address what causes the M3-M6 drop and what product depth fixes it.
Source. Aspire-side cleanup of 2Org_Chart_as_of_05192026 → v2, with role-level adjusted compensation reflecting the proposed Day 1 cuts.
Net effect. ~27 of 100 Aspire heads exited Day 1. Annualized compensation runs from $11.83M → $9.61M. Plus benefits/taxes savings of $0.44M. Total annualized savings: $2.66M.
What's retained. Revenue/Sales (7), Marketing (8), Business Ops (1), Executive (2). VP CS retained at adjusted comp. Strategic Sales Director retained.
| Department | Heads before | Heads after | Comp before | Comp after | Savings | Decision logic |
|---|---|---|---|---|---|---|
| Managed / Agency Services | 35 | 21 | $2.95M | $2.05M | $894k | 14 of 28 Campaign Associates and Managers exit — prep for agentic agency |
| R&D | 17 | 12 | $2.24M | $1.68M | $557k | Eliminate 2 SWE, 2 Sr PM, 1 PM — duplicated by Cirqle product team |
| Customer Success | 18 | ~13-14 | $1.69M | $1.27M | $423k | Quarter cut across CS layer (4-5 roles below VP), VP CS retained at full comp |
| G&A People Operations | 4 | 3 | $445k | $240k | $205k | Sr. Director People Ops eliminated |
| G&A Finance & Accounting | 8 | 6 | $671k | $536k | $136k | Deal Desk Lead + Specialist eliminated |
| Revenue / Sales | 7 | 7 | $2.02M | $2.02M | $0 | Fully retained — Strategic Sales Director + 6 reps |
| Marketing | 8 | 8 | $1.03M | $1.03M | $0 | Fully retained — US brand muscle |
| G&A Business Operations | 1 | 1 | $400k | $400k | $0 | COO retained (transition role) |
| G&A Executive | 2 | 2 | $385k | $385k | $0 | Anand becomes President |
| Total | 100 | ~73 | $11.83M | $9.61M | $2.22M |
| Role | Annual comp | Why |
|---|---|---|
| Senior Software Engineer | $160,000 | Duplicated by Cirqle engineering team |
| Software Engineer II | $140,688 | Duplicated by Cirqle engineering team |
| Senior Product Manager | $62,305 | Duplicated by Cirqle product team |
| Senior Product Manager — AI (India) | $64,382 | Cirqle owns AI roadmap centrally |
| Product Manager | $130,000 | Duplicated by Cirqle product team |
| R&D subtotal | $557,375 |
| Role | Annual comp | Why |
|---|---|---|
| Sr. Director, People Operations | $205,000 | Combined HR led from Cirqle side post-close |
| Deal Desk Lead | $120,000 | Cirqle owns the new revenue model + deal architecture |
| Deal Desk Support Specialist | $15,600 | Same as above |
| G&A subtotal | $340,600 |
14 of 28 Campaign Associates, Campaign Managers, and Campaign Assistants exit. Remaining 14 Campaign roles + 7 leads/specialists = 21 heads retained. Logic: agentic agency tooling will progressively replace remaining Campaign roles in Y2 (target ~14 total by M24).
4-5 of 18 CS heads exited. VP CS retained at full $330k comp as the retention engine. Quarter cut applied to 4-5 CS roles below VP level. Logic: aligns to Cirqle's leaner CS structure while keeping enterprise account coverage intact.
| Component | Annualized | Y1 (with timing) | Y2 (full) |
|---|---|---|---|
| Salary savings | $2,215,583 | ~$1.85M | $2.22M |
| Benefits/taxes (assume 20% load) | $443,117 | ~$370k | $0.44M |
| Total cash savings | $2,658,700 | ~$2.22M | $2.66M |
| Less: severance one-time (30-day) | — | ($185k) | $0 |
| Less: retention bonuses for retained leaders | — | ($800k) | ($400k) |
| Net Y1 cash impact | — | ~$1.24M | $2.26M |
| Month | MRR | Net new |
|---|---|---|
| April 26 | $317k | $49k |
| Implied EOY ARR | $10M target ($500-588k/head at 17-20 heads EOY) | |
Cirqle's NRR is strong — the AI-native architecture and performance-attribution layer drive expansion within accounts as creator and ad spend scales with the customer. The playbook used to deliver this is what we bring to support Aspire's NRR transition from 47% back toward 60%+ steady state.
For the joint financial model: Cirqle retention metrics by cohort will be shared with Leon under NDA for the Session 5 build.
| Line | FY23 | FY24 | FY25 | Jan 26 run-rate |
|---|---|---|---|---|
| SaaS | $11.9M | $11.4M | $11.1M | $10.8M |
| Agency (managed services) | $8.6M | $7.9M | $8.2M | $5.4M |
| Other | $0.0M | $0.6M | $1.0M | $1.6M |
| Total revenue | $20.5M | $19.9M | $20.2M | $17.8M |
| EBITDA | -$6.3M | -$3.2M | -$0.3M | -$3.6M |
| EBITDA margin | -31% | -16% | -1% | -20% |
| Item | Annualized | Note |
|---|---|---|
| Normalized EBITDA today (pre-Q1 hires) | ~$0M | Breakeven baseline |
| +20 Q1 26 hires (cost absorbed) | -$2.4M | 20 heads × ~$120k all-in avg |
| Jan 26 run-rate EBITDA (with hires) | -$2.4M | Investment in growth, not structural loss |
| Less: v2 org cleanup savings | +$2.66M | 27 heads exit, applied Day 1 |
| Aspire EBITDA post-v2 | ~+$0.3M | Returns to positive contribution |
The v2 cleanup substantially offsets the Q1 hire absorption. Net effect: Aspire arrives at Close with a clean breakeven-to-positive contribution, not a -$3.6M drag.
Pattern: Multi-year recovery from FY23 to ~breakeven by FY25. Aspire is at breakeven today on a normalized basis. The Jan 26 run-rate of -$3.6M reflects the +20 Q1 26 hires absorbing as cost, expected to drive future growth. Once v2 org cleanup is applied (-27 heads, $2.66M savings), Aspire returns to positive EBITDA (~$0.3M annualized).
| Item | FY23 | FY24 | FY25 | Jan 26 |
|---|---|---|---|---|
| Cash | $11M | $8M | $6.5M | $5.8M |
| Creator liability | -$10M | -$11M | -$13M | -$14.4M |
| Deferred revenue | ~$3.5M | ~$3.2M | ~$3M | ~$3M |
| Department | Heads | Comp ($M) | Avg comp ($k) |
|---|---|---|---|
| Managed / Agency Services | 35 | $2.95 | $84 |
| Customer Success | 18 | $1.69 | $94 |
| R&D | 17 | $2.24 | $132 |
| G&A (Finance, People, BizOps, Exec) | 15 | $1.90 | $127 |
| Marketing | 8 | $1.03 | $129 |
| Revenue / Sales | 7 | $2.02 | $289 |
| Total | 100 | $11.83 | $118 |
53 of 100 heads are in Managed Services + CS — confirming this is a services-heavy hybrid, not a pure SaaS. Sales avg comp at $289k suggests heavy OTE — confirms US enterprise motion. See Aspire org cleanup v2 tab for the proposed Day 1 plan.
| Class | Shares (M) | Price | LP at 1x |
|---|---|---|---|
| Series A-1 (Hummer Winblad lead) | 13.6 | $0.92 | $12.55M |
| Series A | 18.0 | $0.38 | $6.85M |
| Series Seed | 16.8 | $0.21 | $3.52M |
| SAFE + Convertibles | — | — | $7.82M (post-money/MFN) |
| Total preference + SAFE | $30.74M |
Capital structure summary provided by Aspire. Internal waterfall and allocation across Aspire shareholders is determined by Aspire per term sheet §9. Open item for Session 3 (Org): structure of any retention grants from the 40% NewCo pool for Anand and key Aspire leaders.
| Question | Why it matters |
|---|---|
| 1. Creator float aging | Why is the $14.4M growing? Faster payouts demanded? Determines liquidity at close. |
| 2. "Other" $1.6M run-rate revenue | Affiliate fees? Marketplace transaction fees? Data licensing? Determines marketplace asset value. |
| 3. NRR by ACV band | Is the 47% NRR driven by SMB churn or enterprise losses? Determines if Aspire's CS muscle is real. |
| 4. Professional & Outside Services line | $3.9M is 20% of revenue. Outsourced delivery? Legal? Determines if it's a $1-2M synergy or true variable cost. |
| 5. Change-of-control provisions | Top 20 customer contracts. Determines integration risk and customer churn modeling. |