If you’re looking for a B2B SaaS outbound playbook that actually got used, this is the one I ran as Rippling’s first go-to-market sales development hire in Australia. Rippling is a $16 billion HR and payroll business. When we launched here there were four of us in a co-working space in Sydney and nobody in the local HR or payroll market had heard of us.
Australia went from zero to $10 million. I’m not going to pretend I did that by myself. There was a big inbound channel and a partner network selling behind us. But running cold outbound was my entire job, and it brought in over $7 million in pipeline and over a million dollars in closed-won revenue.
Here’s what the playbook actually looked like.
The playbook from head office didn’t work here
The assumption baked into the US playbook was that Australian buyers cared about the same things American buyers did. They didn’t.
Australian businesses have their own payroll legislation and compliance obligations. Budget cycles ran differently. The competitor set was completely different. And the wording that landed in an American email did nothing for a buyer in Sydney.
We were also up against an incumbent everyone trusted. Employment Hero is the Australian all-in-one HR system and nearly every company we called was already on it. HiBob had been selling here for a couple of years before we showed up. And the week we opened the Sydney office, the founder of Employment Hero gave an interview to the Australian press saying you can’t just drop an American HR and payroll system into Australia and expect it to work.
So the biggest player in the market was actively telling buyers not to trust us.
Your reps are your market research team
We had a messaging problem and no way to solve it from a desk. No analyst report was going to fix it. Our marketing team had never sold into this market.
The only source of truth was the calls we were already making.
Every week, Noah Adelstein, the head of growth for the region, sat down with us and asked the same three questions:
- What are you hearing from our prospects?
- What do they care about?
- What are they saying about our competitors?
Whatever came out of that went straight into the next email sequence, the cold call scripts and the marketing. Then we did it again the following week.
Modern awards is the example I always give. Australia has a whole system of industry-specific pay rules, and Rippling had no visibility of it coming in. We only learned how much it mattered because prospects kept raising it on calls. Within weeks it was shaping how we talked about compliance.
If you have reps dialling right now, you are already running the most expensive market research programme in your company. Most teams just never collect the results. Book 30 minutes a week and ask those three questions.
Build the list around buying signals
Knowing what to say only matters if you’re saying it to the right companies.
I ran LinkedIn Sales Navigator connected directly to Salesforce, so every account I owned showed up inside it automatically. Then I built saved searches for the three things that told me a company might be in the market right now.
New leadership in the buying seat
A new head of HR or head of people and culture starting somewhere. More often than not, that person is evaluating the systems they’ve just inherited.
Hiring activity
A company with a stack of open roles, especially roles that had been open for months. That told me the business was growing and about to start feeling the pain of running everything on separate systems.
Hiring in another country
We sold global payroll. The second a company posted a role in another country, they had a problem to solve about paying those people.
Signals tell you who to call first. They don’t fill a week. You run out of them fast. So on top of the signal accounts I worked through 50 to 100 companies a week whether they’d shown me anything or not. Volume negates luck every single time, and the best reps I’ve seen are the ones making the calls nobody else wants to make.
The list mistake I’d undo
If I could change one thing, it wouldn’t be the script. It’d be which companies went on the list in the first place.
A huge share of Australian small and mid-sized businesses run payroll through Xero. Back then we had no Xero integration, and our payroll product couldn’t handle some of the local compliance requirements yet.
We called them anyway. They’d take the meeting, take the second meeting, sit through a demo. Then late in the cycle someone would ask how we integrate with Xero, and the deal would die.
Every hour spent there was an hour not spent on the part of the market we could actually serve. Build the list of companies you can’t win before you build the list of the ones you want.
Never call one person at an account
Rippling sold HR, payroll and IT device management in a single platform. So I worked backwards from the product: three departments in any given company could care about what we sold.
- HR — head of HR, people and culture manager, people operations, talent acquisition
- Finance — CFO, financial controller, finance manager, head of accounting
- IT — head of IT, IT operations manager
That’s 10 to 12 people in one business. One person telling me no never took the company off the list.
What I said changed with seniority. With a CFO it came down to three things: risk, cost and revenue, and a business case for what happens if the problem never gets fixed. A level or two down, the person is stuck in the weeds with it every day, so with a finance manager I’d talk about the manual work and how slow the current system is to use. Two people in the same company will take the meeting for completely different reasons.
Even a no is worth something. I once called a financial controller with zero interest in meeting who still told me when their renewal was, what systems they were running and what had gone wrong with them. I called the finance manager at the same company next and opened with it. That isn’t a cold call anymore.
Protect the calling block
My minimum was 100 dials a day. We didn’t have parallel dialers back then, so every one of those was me dialling the number myself.
My manager Ron had a rule he called “20 before 10”. Twenty dials before 10am, every day. I’d be in at 8:30, and by the time most of the team had made their first call I was already 20 deep.
I ran the day in blocks so calling had its own protected time. 8:30 to 10:30 non-stop, short break, listen back to a few calls, then straight into the next block. Anything that wasn’t calling, like list building and research, was done the day before or handled inside those saved searches.
Everyone I found went into Outreach, which told me each morning exactly who to call. Those emails weren’t there to book the meeting. They were there so my name wasn’t completely unfamiliar when the phone rang. A buyer used to get about five cold emails a day. They’re now getting 20 to 30, and most of them read identically because they’re written with the same handful of AI tools.
The three motions that ran alongside the phone
Cold calling brought in most of our meetings. Three other things ran beside it, and all three were doing the same job: making us look like we’d been in the market longer than we had.
Getting in a room. We hosted private dinners for HR and finance leaders in Sydney and Melbourne, and sponsored the major HR and payroll events. Nobody signed on the night. The point was that the next time we called that company, they’d heard of us.
Direct mail. Each SDR nominated around 20 accounts a month for a good bottle of wine and a handwritten note. Nothing random about the picks: strong fit on size and industry, or someone who’d already shown interest, visited the site or looked us up on G2. Between 70 and 80% of those accounts became a qualified opportunity, and plenty closed.
Partnerships. After the SDR role I moved into a channel account executive seat, working with the HR consultants and accountants advising the businesses we wanted. There was no Australian playbook for it, so we built it from scratch. Lunches, sales material, a cut of any referral they sent our way. By the time we spoke to those companies, someone they already trusted had put in a good word.
What to take from it
None of this is complicated. It’s a list built on signals, enough volume underneath it to survive the weeks where the signals dry up, multiple people worked at every account, a protected block of time for the phone, and a weekly loop that turns what your reps hear into what your reps say.
The expensive part is the months of calls it takes to work out what actually resonates in your market. That’s the bit you can shortcut.