Dimely

What do they actually do

Dimely builds an AI layer that automates manual billing work on top of a company’s existing spreadsheets and finance stack. It ingests billing documents (contracts, order forms, POs), classifies them, extracts key terms, matches those against structured data from systems like a CRM or data warehouse, flags discrepancies, and surfaces them in a spreadsheet-like review interface and via Slack. When configured, it can sync reconciled results back into finance systems such as Stripe and NetSuite (Dimely site, Fondo launch note).

Today it targets B2B SaaS finance and billing teams—especially mid‑market and enterprise teams with bespoke contracts or usage‑based pricing that still rely on spreadsheets. The product is live, and the company publishes SOC 2 materials for enterprise buyers (YC profile, Dimely site, Trust Center).

Who are their target customer(s)

• Mid‑market SaaS finance or billing manager: Spends hours copying contract terms from PDFs and matching them to CRM/usage data, causing slow month‑end closes and billing errors.
• Revenue operations or billing ops lead at an enterprise/fast‑growing SaaS: Deals with bespoke pricing and approvals; inconsistent contract terms and manual order management lead to missed or incorrect invoices and frequent exceptions.
• Accounts receivable or billing specialist: Must turn contracts into invoices and reconcile payments across systems; repetitive data entry and hunting down discrepancies create delays and mistakes.
• Finance/ops owner for usage‑based or overage billing: Struggles to translate usage metrics into correct charges because data lives in multiple systems and there are no automated checks, leading to disputes.
• Controller or VP Finance moving upmarket: Needs audit‑ready billing and clear revenue recognition trails; current spreadsheet logs are fragmented and hard to audit, slowing compliance and forecasting.

How would they acquire their first 10, 50, and 100 customers

• First 10: Founder‑led pilots via warm intros (YC network and prior SheetWhiz contacts), ingest a small set of contracts, map to CRM/usage, and resolve exceptions together to generate quick wins and references (YC profile, Work at a Startup).
• First 50: Target mid‑market finance/billing managers with SDR/AE outreach offering a short proof‑of‑value (e.g., contracts→invoices or usage reconciliation) and publish brief case studies; emphasize low lift and SOC 2 to smooth procurement (Dimely site, Trust Center).
• First 100: Productize common connectors (CRM, Stripe, NetSuite) and a templated onboarding so sales can close without bespoke engineering; add RevOps/billing services partners and use launch press and niche events to fill top‑of‑funnel (Dimely site, Fondo launch note).

What is the rough total addressable market

Top-down context:

Relevant spend sits within subscription billing/order management ($7.15B in 2024) plus a slice of CPQ (~$5.8B projected by 2026); given overlap, this supports a core TAM in the low tens of billions rather than a sum of both categories (Grand View Research, MGI Research).

Bottom-up calculation:

Assume 10,000–20,000 mid‑market and enterprise B2B SaaS companies with complex, spreadsheet‑heavy billing worldwide, each spending ~$50k–$150k annually on contract‑to‑invoice and reconciliation software—yielding roughly $0.5–$3B serviceable TAM today, expanding as adoption deepens and scope broadens (SaaS company counts context).

Assumptions:

• Targetable buyers are a subset of global SaaS companies (thousands to low‑tens of thousands) with bespoke/usage‑based billing and spreadsheet‑driven workflows.
• Average annual software spend for this function ranges from ~$50k for mid‑market to ~$150k+ for larger enterprises.
• Subscription billing and CPQ budgets overlap; top‑down market figures are not additive.

Who are some of their notable competitors

• Evisort: AI contract management that extracts and normalizes terms from PDFs at scale; overlaps on the document classification/term‑extraction layer (site).
• Zuora: Subscription and usage‑based billing platform handling mediation, rating, invoicing, and revenue automation—an alternative to layering an external reconciliation/review tool (guide).
• Stripe Billing: Subscriptions, usage billing, invoicing, and collections with built‑in reconciliation; mid‑market teams may centralize billing here instead of adding an overlay (docs).
• HighRadius: AR and cash‑application automation that captures remittances, matches payments, and posts to ERPs—competes on reconciliation and ERP posting (product).
• Billtrust: End‑to‑end order‑to‑cash/AR (invoicing, payments, cash application, collections, AP portals); an all‑in‑one AR alternative to a spreadsheet‑centric review layer (overview).