Follow one software subscription from the day you find it to a renewal you chose on purpose. Turn the dial to see what AI takes off your plate at each step, what it hands back to you, and which tools do it today.
Some tools let an assistant like Claude read your software contracts directly. Vertice hosts its own connector, and Tropic is a verified connector in Claude's directory.
Free email course
One lesson every few days, each a four-minute read with one small thing to try that week. It starts with the jobs almost every business has: paying bills, payroll and the month-end close.
The last lesson links back to this walkthrough and the other seven.
Today. Scroll card statements and expense reports once a year and hope you spotted every tool.
With AI. Matches charges, bills and logins to known software vendors and groups them into one subscription list. In: card and bank charges, bills and your sign-in data. Out: one list of every tool, what it costs and who uses it.
Who decides. AI-assisted: AI builds the list, finance confirms each tool. AI-run: New tools join the list on their own, unknown charges go to a person.
Control. Every recurring software charge appears on one subscription list.
Tools that do this. Sastrify (score 65): finds apps through your identity provider and a browser extension, and adds paid tools from ERP bills. Pleo (score 76): vendor cards sit alongside recurring vendor tracking, so each SaaS charge shows as its own line. Mesh Payments (score 72): its MCP connector lets Claude answer questions such as SaaS spend by quarter or idle virtual cards, from live Mesh data.
Today. Nobody owns the tool, so nobody knows the contract terms or who to ask about it.
With AI. Reads each contract for dates, value and renewal terms, and suggests an owner from who bought and uses the tool. In: the subscription list and the signed contracts. Out: each tool with a named owner and its key terms.
Who decides. AI-assisted: AI fills in the terms and suggests an owner, a person confirms. AI-run: Terms are filled in, and tools without a clear owner go to a person.
Control. Every subscription has a named owner.
Tools that do this. Sastrify (score 65): its Contract AI reads a contract PDF and fills dates, value, renewal terms and line items for a person to check. Tropic (score 74): setup starts with contract upload, so Tropic can extract renewal dates, spend and suppliers. Soldo (score 69): dedicated subscription cards keep recurring vendor charges off employee cards and tie them to one owner.
Today. Find out about the renewal when the charge hits the card.
With AI. Builds a renewal calendar, alerts the owner well before the notice deadline, and ranks which renewals are worth a closer look. In: each tool's renewal date and notice period. Out: a renewal queue, ranked, with deadlines in view.
Who decides. AI-assisted: AI alerts the owner, the owner plans the review. AI-run: Small renewals roll into review on their own, big ones go to a person.
Control. No renewal date passes without a review.
Tools that do this. Spendesk (score 75): contract renewal alerts arrive four months and one month before the deadline (procurement add-on). Pleo (score 76): renewal management sits alongside vendor cards on the Optimise plan. Tropic (score 74): its Purchase Prep agent ranks contracts worth negotiating and flags auto-renewal traps.
Today. Renew at the same seat count because nobody checked who still logs in.
With AI. Compares paid seats with active users, finds former staff and overlapping tools, and flags anything off. In: seat counts, sign-in data and who has left. Out: a right-sized seat count, or a flag with the reason.
Who decides. AI-assisted: AI checks, the owner reviews every gap. AI-run: Matching counts pass, unused seats and overlaps go to a person.
Control. Seats are checked against active users before every renewal.
Tools that do this. Sastrify (score 65): its browser extension shows which apps people actually open. Tropic (score 74): its Purchase Prep agent surveys stakeholders on usage as part of renewal prep. Vertice (score 77): its SaaS Purchasing service includes usage analytics and renewal visibility alongside expert negotiation.
Today. Accept the vendor's renewal quote because there is nothing to compare it with.
With AI. Compares the quote with benchmark prices and your own history, and drafts a negotiation plan and emails. In: the renewal quote, your seat count and price data. Out: a target price, a script and draft emails.
Who decides. AI-assisted: AI drafts the plan, the owner runs the talks. AI-run: AI runs routine rounds, a person reviews each one.
Control. Nothing is agreed with a vendor without a person's yes.
Tools that do this. Tropic (score 74): its Proposal Review Agent reads an uploaded quote and returns a savings estimate, a difficulty rating and a script. Sastrify (score 65): an IT buyer reviews unit prices, volumes, payment terms and renewal clauses before a renewal. Vertice (score 77): its AI negotiator drafts and sends negotiation emails in your voice, with or without a person reviewing each round. Zip (score 80): its Price Negotiation Agent compares a renewal with your own history and Vendr's pricing data and suggests tactics.
Today. The renewal goes through by default because nobody said no in time.
With AI. Summarises seats, usage, price and notice terms on one card and routes it to the owner and approver. In: the usage check, the benchmark and the contract terms. Out: a renew, resize or cancel decision with the facts in view.
Who decides. AI-assisted: A named owner and approver decide, with the facts in view. AI-run: A named owner and approver decide, always.
Control. A person signs every renewal and cancellation, and AI never signs a contract.
Tools that do this. Sastrify (score 65): routes new purchases and renewals through sequential or parallel approval stages with named approvers. Ramp (score 85): the Procurement add-on routes parallel approvals to finance, IT and legal. Tropic (score 74): under its MSA, Tropic acts only as a limited agent and cannot sign on your behalf.
Today. The tool bills a shared company card, so cancelling it means cancelling the card for everyone.
With AI. Issues or updates a card locked to that one vendor, capped at the approved amount, and blocks charges that don't match. In: the approved renewal and its price. Out: a payment that matches the decision, and a card you can kill alone.
Who decides. AI-assisted: AI sets up the card, finance confirms it. AI-run: Matching charges go through, anything off is blocked for a person.
Control. One card per vendor, locked to that vendor and capped at the approved amount.
Tools that do this. Pleo (score 76): vendor cards lock to one merchant, and finance can kill one without touching anyone else's spend. Mesh Payments (score 72): a subscription card per vendor is locked so it cannot be used anywhere else. Volopay (score 65): issue a virtual card per tool, cap it, and set an auto-block date. Ramp (score 85): card controls block spend by merchant, category and amount before it happens.
“Do we already pay for a design tool? I need one for the new hire.” Searches the subscription list, checks seats against active users and names the owner. AI-run sends the answer. AI-assisted drafts it for finance.
“Your renewal is in 30 days. Can we confirm the same 50 seats at this year's price?” Pulls the usage check and the benchmark into a draft reply and sends it to the owner. The tool's owner, who decides and replies.
“Can I put a new AI notetaker on my own card and expense it? It's only $30 a month.” Never approves software bought around review. Opens a request and routes it to the approver. The approver, always.
Tools that do this. Tropic (score 74): with its Claude connector, Claude can search contract language such as auto-renewal clauses and list contracts. Vertice (score 77): with its MCP connector, Claude can list contracts expiring in the next 90 days and asks before opening a purchase request. Sastrify (score 65): a Jira app lets tool owners raise procurement requests without logging in. Zip (score 80): employees file purchase, vendor and renewal requests in one place, and each routes to the reviews it needs.
Put in your own figures. The result is labour only, and you choose how much of the work you expect AI to take on.
We don't show an industry benchmark here, because we haven't found a current, independent figure for what managing software subscriptions costs.