# Monthly to annual: when to offer annual prepay and what to log in Pipedrive

https://salesbond.app/blog/annual-prepay-offer-monthly-customers-pipedrive/
Published: 2026-10-07 · Updated: 2026-10-07

Offer the switch from monthly to annual prepay after the first result you and the customer can both point to, usually between month three and month six, and only to customers who use the product and pay on time. Run the offer as its own deal in Pipedrive with an offer date and a recorded answer. Without that record you will never know whether the discount was worth the cash that came in early.

## Three months, five invoices and one email

Anselm sells document scanners and the subscription that goes with them, a team of six, about 60 accounts. Fourteen of those accounts pay monthly. (The numbers in this article are an example.) In April his accountant asked whether sales could “just move them to annual”. So Cordelia, who looks after existing accounts, wrote one email, sent it to all fourteen on the same Tuesday, and offered everyone two months free for paying the year up front.

Two accepted. One replied asking whether something was wrong with the company’s cash position. One, whose scanner had been in for repair twice that quarter, took the email as a cue to reread the contract and cancelled at the end of the month. The other ten did not answer and nobody wrote down who had been asked, so when Cordelia raised the idea again with one of them in September, the customer said “you already asked me this and I said no”.

The discount was ordinary and the idea was sound. What failed was the selection, the timing and the missing record. The fix is a handful of conversations with the right customers at the right moments, logged like any other deal.

## Who not to offer it to

Skip monthly customers who paid late, have an open complaint or downgrade, use little, or joined under three months ago. Check the account in Pipedrive before anyone picks up the phone:

- A payment in the last three months went out late or needed a reminder. Asking for twelve months up front from someone who struggles with one is a strange request.
- There is an open complaint, a support ticket that has been bouncing, or a product that came back for repair. The customer is deciding whether to stay, and an annual ask forces that decision early, in the wrong direction.
- There is an open or recent downgrade conversation. A customer who asked to reduce seats last month is a [downsell case](https://salesbond.app/blog/downsell-customer-downgrade-pipedrive/), not an annual-prepay candidate.
- Usage is low. If they bought ten licences and three are active, the annual price looks like a bill for seven things they do not use.
- They have been a customer for under three months. There is no result yet for either side to point to.

[SaaStr](https://www.saastr.com/how-do-i-convince-saas-customers-with-monthly-plans-to-upgrade-to-annual-plans) warns against breaking the way a customer already buys. They name MongoDB and Zoom as companies where pushing annual too hard reduced sales, and they would put real effort into the switch only for customers worth more than $10,000 a year. We’d set the bar lower for a six-person team, but the principle holds: a small customer happy paying monthly is not a problem to solve.

We build SalesBond, a sales management layer on top of the CRM a team already uses; we started with Pipedrive. Its Customer Health module works out a buying cycle from won deals, and a cycle needs at least two purchases, so for a subscriber on a single recurring deal the selection above is done by hand, with a filter and ten minutes. [Check your CRM with SalesBond](https://salesbond.app/) to see which repeat customers are already late; [customer health without a score](https://salesbond.app/blog/customer-health-score-pipedrive/) is a separate article.

## When to offer the switch from monthly to annual

The right moment is the first time the customer tells you, in their own words, that the thing works. Cordelia’s best candidate was Florian, a logistics firm that had put the scanners into a second warehouse in month four and emailed to ask about adding a third. That email is the moment. The customer has just confirmed value out loud and is about to spend more with you anyway, so the annual conversation extends one they started.

A consumables reorder or a quiet quarterly check-in counts too: the customer did something that says “we are staying”.

Month counts matter less than the moment, but they help you not forget. SaaStr suggests raising annual with active customers 50 to 90 days in. Fungies, writing for self-serve products, lands on an email at month three and a second one at month six ( [Fungies, April 2026](https://fungies.io/annual-vs-monthly-saas-pricing-strategy/)). Where a person owns the account, we treat month three as the earliest date to start looking for the moment, not as a date to send anything.

Three days are off limits. Not the day the invoice goes out, because an offer that arrives with a bill reads as a collections tactic. Not the day of a price increase, because the customer will hear “lock in before it gets worse”; [a price increase with existing customers](https://salesbond.app/blog/price-increase-customers-pipedrive/) is its own job. And not inside the [renewal window](https://salesbond.app/blog/customer-renewal-process-pipedrive/) of a customer whose term is already ending, where the question is whether they stay at all. Annual prepay is a question for a customer who is not going anywhere.

![Timeline of a monthly customer's first eight months: three moments to offer annual prepay, three days to avoid, earliest month 3](https://salesbond.app/wp-content/uploads/2026/10/annual-prepay-offer-monthly-customers-pipedrive-2.png)

## What to say: the price for the year, not the percentage

Say the number. “Your subscription is $400 a month, so $4,800 a year. If you pay the year up front it is $4,000, invoiced once, and nothing else changes.” (Example figures.) The customer hears what they save and what they are being asked to find in one go. “Seventeen percent off” makes them do the arithmetic, and the first thing they’ll do with it is check whether the monthly price is padded.

Then say what they give up, before they ask. They give up the the ability to stop next month. For a customer who has just put scanners into a second warehouse, that is not much of a loss, and saying it out loud keeps the conversation from feeling like a trap. If they hesitate there, that’s useful information: they are less committed than the second warehouse suggested, and the right answer is “no problem, stay monthly, I will ask again in the spring”.

How big a discount? Sources run from two months free, about 16 to 17 percent, which [Monetizely](https://www.getmonetizely.com/faqs/what-kind-of-discount-should-we-offer-for-annual-prepayment-versus-monthly-is-the-typical-approach-to-give-2-months-free-about-16-17-off-or-do-some-companies-do-a-different-discount-for-yearly-plans) calls the common approach, up to the 20 to 30 percent SaaStr suggests. We use two months free because it is easy to say on a call, and we write it down once as a rule so no rep invents a discount per customer; the [discount policy article](https://salesbond.app/blog/discount-policy-sales-teams/) covers how. If the customer asks about two or three years, that is a different negotiation, covered in [multi-year deals](https://salesbond.app/blog/multi-year-deals-pipedrive/). Don’t improvise it on a call about annual.

## What to log in Pipedrive

The offer is a deal, not a note or a tag, because a deal has an owner, a stage and an outcome, and the point is to count outcomes later. Pipedrive has no built-in “annual switch” object, so this is a convention you set up once.

Put it in the pipeline where existing-customer work already lives (renewals, upsells); if there is none, create one called Customers with three stages: Candidate, Offered, Answered. Name the deal “Annual switch: “.

Keep it out of your revenue numbers. If the subscription already sits on the customer’s original won deal as a recurring product, that is where the revenue is counted, and an Annual switch deal closed as Won at $4,000 would show up in won-deal reports as new sales on top of it. So leave the switch deal’s value at zero and filter the Customers pipeline out of any new-business report. The deal records a conversation, not money; [ACV vs deal value](https://salesbond.app/blog/acv-vs-deal-value-pipedrive/) explains why those two numbers are kept apart anyway.

Four custom fields on the deal do the recording. These are your own fields; none of them exist in Pipedrive out of the box.

- Billing term: a single-option field, Monthly or Annual prepay. Set to Monthly when the deal is created, Annual prepay when the customer switches. Filter on it and you have the candidate list at any moment.
- Offer date: the day the customer actually heard the offer. Not the day you decided to offer, not the day the deal was created. A deal with no Offer date has no place in the count, whatever it’s stage says.
- Answer: a single-option field with four values. Accepted. Prefers monthly. Declined. No reply. “Prefers monthly” and “Declined” are different answers: the first customer is happy and wants flexibility, the second has a reason, and the reason goes in the notes.
- Ask again on: a date field. Every “Prefers monthly” and every “No reply” gets one. Six months is our default.

The outcome lives in the deal status, not in a stage. Won when the prepay invoice is paid, not the day the customer said yes. Lost, with the reason, for a Declined. “Prefers monthly” and “No reply” stay open in Answered until the Ask again date; a yes that never turns into a payment becomes a “Prefers monthly” with a new date.

The billing change itself belongs on the subscription. Pipedrive works out MRR and ARR from recurring products, each with a billing frequency such as monthly or annually, on Growth plans and higher ( [Pipedrive: recurring products](https://support.pipedrive.com/en/article/recurring-products)). So the new price and term go on the customer’s recurring product, not into a second deal value; the mechanics are in [recurring products vs installments](https://salesbond.app/blog/pipedrive-recurring-products-vs-installments/).

If a whole pipeline feels heavy for fourteen accounts, an activity type called Annual offer with the same four facts in the note will do, but you lose the conversion report, which is the thing you were trying to get.

![Generic deal card "Annual switch: Florian Logistics" at the Answered stage with four custom fields and a short note](https://salesbond.app/wp-content/uploads/2026/10/annual-prepay-offer-monthly-customers-pipedrive-3.png)

## How to count whether it worked

Did the offer pay for itself? Count by cohort of offers, not by month of revenue. Everyone who heard the offer in a given quarter is one cohort; the rate you care about is accepted divided by offered, and the second number is what happened to the people who said no.

Cordelia’s second attempt, with the selection and timing above, looked like this. (Example, numbers illustrative.)

| Quarter cohort | Count | What it tells you |
| --- | --- | --- |
| Monthly customers at start | 14 | the pool |
| Passed the filter | 5 | how strict the filter is; too few means loosen it, too many means it is not a filter |
| Offered (Offer date set) | 5 | the denominator; a candidate never offered is a timing failure, not a customer failure |
| Accepted, prepay paid | 3 | the acceptance rate, here 3 of 5 |
| Prefers monthly, Ask again set | 2 | the follow-up list for next cohort |
| Declined with a reason | 0 | if this grows, the filter is letting unhappy accounts through |
| Cancelled within 60 days of the offer | 0 | the number that says the offer itself did harm; anything above zero needs a look |

Then the money. Three customers at $400 a month would have paid $14,400 over the year if all three stayed every month. They paid $12,000 up front instead, so the discount cost $2,400. What it bought is twelve months of certainty on three accounts and thirty-three fewer invoices. If none of your monthly customers ever leave the discount was a gift. Now suppose one of the three would have cancelled after six months: monthly billing would then have brought in $4,800 + $4,800 + $2,400, the same $12,000. One early cancellation among three is roughly break-even. Pull your own rate from the last twelve months of cancellations; no industry number will give it to you for a six-person team selling scanners.

Look at the cohort again a year on, at the first annual renewal. If the three renew annually, the acceptance rate was real. If they ask to go back to monthly, the discount carried the switch, not the relationship.

## When no is a normal answer

Two of Cordelia’s five said they preferred monthly. One of them was Florian, whose second warehouse was running but whose finance team wanted to see a full quarter of volumes before committing a year. That is not a lost deal. It is a customer telling you, politely, when to ask again, and the deal now says December in Ask again on.

The temptation after a no is to sweeten it: an extra month free, a longer term at a bigger discount. Don’t. The customer has just told you flexibility is worth more to them than the discount, and raising it says you did not hear that. Leave the price where the policy put it, thank them, and let teh date field do the follow-up.