Product

RECOMMENDED

FREE TRIAL

Integrations

UNIFIED CONNECTIONS

View all your subscriptions together to provide a holistic view of your companies health.

Resources

How we generated a $14,000 influx of cash in 7 days

By Josh Pigford on December 08, 2015
Last updated on April 24, 2026

Cash flow is the movement of money into or out of a business, and having a steady and substantial amount of it is crucial for growth and development. When you’ve got a significant amount of cash at your disposal, you can invest in hiring, customer acquisition, and other activities that drive business expansion. We recently tried something that got us an extra $14,000 in cash in seven days, and we'll explore how we achieved this influx.

So, what’s great about subscription businesses is the relative stability. You get a steady-ish stream of revenue that slowly increases over time and is much less susceptible to the whims of other business models that are based on one-off payments.

But what can be slightly frustrating is the “slowly” part. Many times, those customers will be paying you every single month for years, yet you have to patiently wait for that money to trickle in. Or do you?

What if you could get the benefits of a pile of cash and the stability of knowing your customer will be around for longer than a month? Well, my friend, you can, thanks to one thing: annual subscriptions. They’re the magical unicorn of the SaaS world.

There’s a catch, though. The way most companies approach annual plans is to just slap it on their pricing page and hope the customer picks it over the monthly option, maybe enticing them with a little discount.

That’s the passive way to make yourself feel good about “doing something” but I guarantee you’re leaving money on the table.

The annual upsell

Instead of thinking of your annual plan as just a different payment option, think of it as a feature to upsell. “Sell” is the operative part of that word. It requires a little bit of work, but if you do it right, it will pay off.

For nearly two years we’ve been prompting users, via email, to switch to annual a few months in to their subscription. Unfortunately the results were always a bit dismal, with the average conversion rate to annual being around 4.75%.

Here is the contents of that email…

On the surface that looks like it’d potentially work just fine. It highlights the benefits and makes it a quick, self-serve “click the link and be done!” switch. But it always felt a bit too salesy, so I decided to try something a bit more personal and informal.

How’d this puppy perform? The conversion rate on this email is 11%…a whopping 131% increase! It generated over $14,000 in revenue in the first seven days. That’s the stuff you write home about!

There are a number of things different about this email.

  • A 3-month discount, instead of 2
  • Manual process — No one-click, self-serve switch process
  • Personal — Doesn’t include automated “here’s how much you’d save” info
  • Urgency — “We’re testing this out and only offering it to a subset of customers” (which is true, we don’t offer this to lower paying plans)

The open rates were basically the same between the two emails, so subject line didn’t seem to matter. Ultimately, the combination of urgency, personal touch, and a bit larger discount pushed this one over the edge.

I do think the additional discount played a role in increased conversion, but from talking with other founders, most tests point to the size of the discount actually not being that big of a deal.

Future testing

The problem with this format is that it’s not really repeatable over the life of the customer. I suppose you could send it to them once a year, but then the “urgency” factor gets lost.

Testing out a series of these emails is certainly worth our time, as is testing out the size of the discount itself (number of months, percentage discounts, etc).

What are some things you’ve tried to increase annual subscriptions? Any formats you’ve found work really well?

Frequently Asked Questions

  • What is an annual plan in SaaS and why does it matter for cash flow?
    An annual plan is a billing option where subscribers pay for a full year upfront instead of monthly, giving SaaS businesses an immediate cash injection and stronger retention signals.

    For subscription businesses, the difference between annual and monthly billing goes beyond payment frequency. Annual contracts convert future recurring revenue into present-day cash you can deploy right now, whether that means hiring, paid acquisition, or product investment. Customers on annual plans also churn at meaningfully lower rates because they have more skin in the game. The catch is that simply listing an annual pricing option on your pricing page is not enough. Proactively selling the switch to existing monthly subscribers, with a clear discount and a personal touch, is what actually moves the needle on annual plan adoption.
  • How do you increase annual plan conversion from existing monthly subscribers?
    The most effective way to increase annual plan adoption is to treat it as an active upsell to monthly subscribers, not a passive pricing page option.

    A personalised, plain-text email from a founder or account lead consistently outperforms automated upgrade flows. The elements that drive conversion are:
    • A compelling discount framed as free months rather than a percentage off
    • A manual switch process where the customer replies and someone handles it for them, which signals genuine attention
    • Urgency, such as a limited-time offer or availability restricted to a subset of customers
    • A warm, informal tone instead of a templated sales email
    Baremetrics data from this exact test showed an 11% conversion rate using this approach, a 131% improvement over a standard automated email offering two months free.
  • Annual plans vs monthly subscriptions: which is better for reducing churn in SaaS?
    Annual subscriptions reduce churn more effectively than monthly billing because customers commit to a longer billing interval, removing the monthly cancellation decision entirely.

    With monthly billing, every renewal is a small churn risk. Annual contracts shift that risk window to once per year, giving your team more time to demonstrate value and build stickiness before the renewal conversation. Beyond churn rate, annual plans also eliminate a category of involuntary churn caused by failed monthly payment retries. Baremetrics Recover handles failed payment recovery automatically, but fewer monthly billing cycles means fewer opportunities for card failures to interrupt revenue in the first place. For SaaS businesses targeting higher LTV, moving customers from monthly to annual billing is one of the highest-leverage levers available.
  • How do you measure the impact of switching customers to annual billing on MRR and ARR?
    When a monthly subscriber converts to an annual plan, it affects how you record MRR: the upfront cash is real, but MRR should reflect the monthly equivalent of the annual contract, not the lump sum.

    This distinction matters for accurate forecasting. A customer paying $790 per year contributes roughly $65.83 to MRR, the same as their $79 monthly plan, but the cash is in your account now. Tracking this correctly means separating cash flow from recognised recurring revenue. You also want to monitor:
    • The share of your subscriber base on annual vs monthly plans over time
    • Churn rate by billing interval to confirm annual customers retain better
    • Expansion MRR potential if annual customers upgrade at renewal
    Baremetrics breaks down MRR by customer segment so you can track exactly how annual plan adoption shifts your revenue mix without manual spreadsheet work.
  • What discount should you offer to encourage SaaS customers to switch to annual billing?
    The most common annual plan discount is two months free, equivalent to roughly 17% off, but tests suggest a three-month offer can significantly lift conversion without destroying margin.

    The size of the discount matters less than most founders expect. What drives annual plan adoption is how the offer is framed and delivered, not the exact percentage. Framing the discount as free months rather than a percentage tends to feel more tangible to subscribers. A manual, personalised offer from a founder or team member also outperforms a self-serve automated flow, even at the same discount level. If you are running your own pricing experiments, track the resulting changes in MRR, cash collected, and annual vs monthly plan mix in your subscription analytics dashboard so you can measure the real revenue impact of each test.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.