datatools-dev/docs/PLAN.md

Strategic Plan — DataTools

Creator-only. Locks the "what next" in light of the locked criteria (DECISIONS.md §1) and the v1.6 honest status (BUSINESS.md §13). Version: 1.0 · Adopted: 2026-05-01 · Owner: Michael

This document is the active plan, derived from the strategic review of 2026-05-01. It compresses the eight strategic moves and a 90-day execution sequence onto one page so the next decision (build vs. ship vs. market) has a single reference.

It is not a re-lock of operating criteria — those still live in DECISIONS.md and have not changed. This plan is downstream of those criteria; if a move below conflicts with §1 of Decisions, the criteria win.

1. Frame

Locked context (BUSINESS.md, DECISIONS.md):

• Niche Python automation tools, $49–79 single / $149 suite.
• Cash budget ≤ $1,200/mo recurring · Time ≤ 10 hr/wk · No external funding.
• Async + no-touch sales (revisit at $5k/mo MRR).
• Marketplace-first distribution (Gumroad / Lemon Squeezy).
• Streamlit GUI + CLI dual interface, runs locally.
• Lifestyle cashflow goal (no exit needed).

Honest current state (2026-05-01):

Asset	State
Tools 1–5 (Find Duplicates, Clean Text, Standardize Formats, Fix Missing Values, Map Columns)	Ready · 1,691 tests passing · 0 xfailed
Tools 6–9 (Find Unusual Values, Combine Files, Quality Check, Automated Workflows)	Coming Soon
PyInstaller installer pipeline	Not started
macOS code signing (Apple Dev Program)	Not started
Hosted browser demo (Streamlit Cloud)	Not deployed
Landing page	Not live
Marketplace listing (Gumroad)	Not listed
Paying customers	0

Diagnosis: the bottleneck is not feature count — it's distribution. The next $1 of value comes from closing the gap between "code-complete" and "buyer-pulls-out-card", not from tool 6.

2. The eight strategic moves

Numbered moves. Each is consistent with locked criteria.

2.1 Freeze new-tool development (one exception). Ship what exists.

Tools 6–8 are blocked behind a distribution gate: no work on them until the existing 5 tools have a paying customer + one external review (BUSINESS.md §4 sequence rule, applied recursively inside the bundle).

Exception granted 2026-05-01: Tool 09 Automated Workflows is built now. Rationale: the pipeline transforms the bundle from "5 tools you buy" into "an automatable workflow you depend on." That conversion is what produces retention and word-of-mouth — the only marketing channel that scales under the no-network/no-touch constraint.

Parked behind the freeze: post-launch tool ideas are captured in docs/FUTURE-TOOLS.md with feasibility, GUI sketch, effort estimate, and ship criteria for each. Currently parked: #10 PDF → CSV extractor (bank statements et al.) — gated on a paying customer + ≥3 paying customers or ≥5 demo emails explicitly asking for PDF extraction, with the bookkeeper niche converting at least one customer first. None of those triggers have fired yet.

2.2 The demo is the product. Make it embarrassingly good.

• Three persona-tagged sample datasets, not one generic CSV: Shopify customers / bookkeeper bank export / agency lead list.
• Run the full pipeline on the sample (Review → Dedup → Text Clean → Format → Missing → Column Map). Free version caps output rows, not the experience.
• Embed the demo as an iframe on the landing page (not "click to open"). Friction kills conversion.
• Persistent CTA after demo: "Run this on your own 50 k-row file → buy for $49 →" directly above the Gumroad button.

2.3 Niche down. Stop selling "data cleaning."

One engine, three landing pages:

Persona	Landing-page lead	Demo dataset
Shopify operator (priority: pet supplies)	"Clean your customer / vendor / subscriber exports"	uc01_shopify_customer_list
Bookkeeper / freelance accountant	"Reconcile bank exports + vendor lists. Auditable changes."	uc06_bank_export_overlap
Marketing / RevOps agency	"Dedupe lead lists. Standardize phones across vendors."	uc13_combined_lead_sources

Generic copy competes with pip install pandas. Vertical copy competes with nothing.

2.3a Top pain points per niche

The "what does this actually fix?" question. Each pain point below is sourced from operator-domain knowledge of these markets and the buyer-use-case research already captured in BUSINESS.md §4a. Pain points are ranked by frequency × dollar impact for that persona — high-frequency / high-cost pains lead the landing-page copy and the demo dataset.

Validation gap (honest disclaimer): these pains are derived from operator knowledge of the categories, not from a sample of buyer interviews. Per BUSINESS.md §8 (no-touch constraint review at $5k/mo MRR), validate the top-3 per persona via 5 buyer interviews before the first $200 of paid acquisition spend. If any pain ranks below the assumed level, swap it for the next-highest in this list.

Shopify operator (priority: pet supplies)

#	Pain	$ / time impact	Tools that fix it
S1	Klaviyo / Mailchimp / Omnisend per-contact billing. Subscriber list with 10–18 % duplicate rate (case drift, plus signs in Gmail addresses, multiple devices) → recurring overpay forever.	$30–300/mo per percent of dupes on a 50 k list — recurring	Dedup + Format Standardize (email canonicalization) + Pipeline (re-run weekly)
S2	Product feed rejected by Google Merchant Center / Meta Catalog. Smart quotes in titles, NBSP in SKU, inconsistent attributes; campaign launch delayed 24–72 h while feed gets fixed.	1–3 days delayed launch × campaign value	Clean Text + Standardize Formats
S3	Multi-channel order consolidation. Shopify + Etsy + Amazon + Faire + wholesale spreadsheet, each with a different column for "customer email" / "order total" / "ship country".	4–8 hr / month manually merging	Map Columns + Find Duplicates + Automated Workflows
S4	Subscription identity fragmentation. Pet-box subscribers cancel and re-sub under a different email; cohort analysis says churn is 20 % when it's actually 12 % — pricing decisions wrong.	Mis-priced LTV → over- or under-paid acquisition	Dedup with merge=true survivor
S5	International tax / VAT MOSS compliance. Country column is UK / U.K. / United Kingdom / GB in the same export; VAT report breaks. Phone formats per region break call-center routing.	Compliance penalty risk + ops friction	Standardize Formats (per-row country) + Map Columns

Bookkeeper / freelance accountant

#	Pain	$ / time impact	Tools that fix it
B1	Bank-export month-overlap re-import. Same transaction posts twice when Jan and Feb exports overlap at the boundary; client's books understate cash by 1–4 %.	2–4 hr / month / client + reconciliation errors	Dedup with explicit Date+Amount+fuzzy Vendor strategy
B2	QBO / Xero vendor consolidation for 1099 reports. "Amazon" / "amazon.com" / "AMAZON.COM*4F2X9" become 3 vendors; 1099 reports break, P&L by vendor unusable.	1–2 hr / 1099 cycle + IRS-paper-trail risk	Format Standardize (name canonicalization) + Dedup
B3	Liability / professional indemnity. Cannot use AI tools that don't show their work; client audit response window is 24–48 h.	Per-firm liability premium ≈ $500–2,500 / yr	Audit log built into every tool — every change row-logged
B4	Per-license-not-per-client economics. Most cleanup tools are per-seat / per-client SaaS; bookkeepers managing 10–30 clients hit price walls fast.	$30/mo × N clients vs. $49 once	Desktop license, no per-client constraint
B5	Multi-currency books. US-domiciled clients with EU customers; comma-decimal amounts (€1.234,56) crash standard parsers; parens-negative (($89.50)) treated as positive.	30–60 min per multi-currency client per month	Format Standardize (currency_decimal=auto, parens-negative)

Marketing / RevOps agency

#	Pain	$ / time impact	Tools that fix it
R1	HubSpot / Marketo / Iterable per-contact tier pricing. 10 k contacts → enterprise tier at $4–8 k/mo. Every duplicate is a recurring tax.	$200–800 / month per 1 k duplicate contacts — recurring	Dedup with cross-source merge + Pipeline
R2	Email-deliverability / sender reputation. Sending to invalid or duplicate addresses tanks reputation; recovery takes weeks.	Catastrophic — entire email programme degraded	Format Standardize (email canonicalization) + Missing (sentinel detection)
R3	GDPR / contact-data privacy. Uploading lead data to a third-party cleaning SaaS is itself a GDPR concern; legal review blocks adoption.	Compliance risk + 4–8 wk legal-review delay	Local-only desktop app, zero outbound calls
R4	Multi-vendor lead-source unification. Apollo, ZoomInfo, LinkedIn Sales Nav, manual scrapes — each export has different headers, scoring, country format.	1–3 days per campaign of manual unification	Map Columns (alias matching) + Standardize Formats (per-row country) + Find Duplicates
R5	Suppression-list management across 5+ platforms. Each platform has its own format; un-deduped suppression lists let opt-outs slip through, triggering CAN-SPAM / GDPR exposure.	Compliance risk + churn-back cost	Pipeline saved as JSON, re-run on each new suppression batch

2.4 Operationalize the moat the docs already name.

Three durable advantages, each promoted from buried feature to landing-page H1:

• Quality: 1 GB international standardization in ~2.5 minutes, locally. Excel can't do this; OpenRefine fights you for an hour.
• Privacy: "Your data never leaves this computer." Already in the GUI footer — promote to landing-page lead, screenshot the empty network tab.
• Update cadence: ship a v1.1 patch within 30 days of v1.0 launch. Not features — evidence the product is alive. "Added Czech Republic phone format support" beats "no updates in 6 months" every time.

2.5 Surface the audit-trail feature in sales copy.

Every tool has a structured audit log. Most cleaning tools do not. Bookkeepers and consultants get fired if they can't show what changed to a client. The audit feature is currently invisible on every proposed landing page and should be the second-largest callout — right after "runs locally."

Copy seed: "Every change auditable. Hand the audit CSV to your client with the cleaned file."

2.6 Automated Workflows is the retention multiplier.

A buyer with a saved pipeline isn't a one-off purchase — they're a recurring user who recommends the product. This is exactly the behavioural lever the no-touch constraint needs (DECISIONS.md §8 trigger). Build it now (see §2.1 exception).

2.7 Add a $199 "priority support" tier post-launch.

Same code, async-email SLA (24 h response). Targets the bookkeeper / consultant persona whose own time is $300/hr. Zero new product work, ~3× ARPU on 5–10 % of buyers. Lock the SLA to async only so the no-touch constraint isn't violated. Defer until $5 k/mo MRR (the same trigger DECISIONS.md §8 already names).

2.8 Dependency-aware pipeline UX.

Tools have soft execution-order preferences (Text Clean before Format Standardize, Format before Dedup, Missing before Dedup). Automated Workflows recommends the order, warns on reversals, and never forces — the user owns their workflow. Implementation: see src/core/pipeline.py SOFT_DEPENDENCIES.

3. 90-day execution sequence

Week	Action	Done when
1	PyInstaller pipeline · Mac/Win unsigned installers · Apple Dev Program enrollment (1–2 wk lead)	dist/datatools-mac.dmg and dist/datatools-win.exe install on a clean machine
2	Demo deployed to Streamlit Cloud · landing page v1 with embedded demo · 3 persona datasets in the demo	Public URL serves a working pipeline run on a sample dataset in < 30 s
3	Gumroad listing live · share value-first in 3 niche communities (no pitch) · 1 long-tail SEO post for the lead persona	First listing impression captured · post not removed for self-promotion
4	Automated Workflows v1.0 shipped (this week, 2026-05-01 — exception per §2.1) · v1.1 patch announced with Tool 09 + intl improvements	Pipeline saves/loads JSON · 3 demo pipelines preloaded
5–8	Bookkeeper landing page · agency landing page · second tool's promo cycle · priority-support tier added (defer purchase until §2.7 trigger)	Three live landing pages with distinct H1, demo dataset, conversion target
9–13	Tool 06–08 only if revenue trajectory supports continued investment · otherwise more market work on the existing 5 + 09	Decision made on 13 Aug 2026 with revenue data, not feature ambition

4. Decision triggers (re-evaluation prompts)

These flip the plan, not the underlying criteria:

Trigger	Reaction
First paying customer in week 4–13	Continue. Plan is working.
Zero paid in 90 days	Audit the funnel. Demo conversion? Niche fit? Price? Don't add features.
$5 k/mo MRR	DECISIONS.md §8 trigger fires: revisit async + priority-support tier.
Marketplace policy / shutdown	Switch to own-domain Stripe immediately; landing pages are already self-hosted.
Streamlit hard direction change	Low-probability re-lock per DECISIONS.md §8. Tk fallback is documented.

5. Anti-temptations (things the plan refuses)

• More tools before more buyers. Locked. Exception only for Automated Workflows per §2.1.
• SaaS pivot. Recurring infra conflicts with the lifestyle constraint (DECISIONS.md §4).
• Live chat / sales calls. Conflicts with no-touch (DECISIONS.md §1 #8).
• Custom integrations / one-off consulting. $300/hr looks tempting; breaks the "build once, sell many" model that justifies the entire strategy.
• Going broad on personas. "All small businesses" is a generic landing page that converts at 1 %; "Shopify pet-supply operators with 1k–50k customers" converts at 5–15 % in the right communities.

6. What this plan deliberately leaves open

• Whether tools 06–08 ever ship. Decided on revenue, not roadmap.
• Whether to add a fourth niche landing page. Decided on which of the three is producing.
• Whether to invest in own-domain SEO. Compounding 6–18 mo asset; not the early-stage channel. Revisit when marketplace + community produces baseline traffic to optimise.
• Whether to add a Notion / Slack support community. If support volume per 100 sales > 10 (BUSINESS.md §12 target), revisit; else leave async-email only.