How to Hire a Virtual Assistant for Appointment Setting

I run a B2B consulting firm with 22 people, account managers, analysts, and a small but scrappy sales team. And for the first four years of running this business, appointment setting was nobody's job. Which, if you think about it, means it was everybody's job. And we all know how that ends.

In Q3 of 2022, we did a pipeline audit. I was expecting some gaps, not a disaster. What we found was 340 warm leads sitting untouched in our CRM. Some of them were six months old. Six. Months. My sales reps were buried in active deals. My account managers didn't have the bandwidth. Nobody dropped the ball intentionally; the system just had no one responsible for this specific job. Conservative estimate: $40,000 in pipeline, just gone.

That's when I finally hired a virtual assistant for the appointment setting. And I am not going to pretend I got it right immediately, because I didn't. But I will tell you everything I learned so you don't waste the time I did.

My first appointment with an appointment-setting virtual assistant was a generalist. Competent, responsive, good attitude. But the appointment setting was one of ten things on her plate, and it showed. I handed her a lead list, pointed to the calendar tool, and assumed she'd figure it out.

She didn't, and honestly, that was on me.

She didn't know our ICP well enough to qualify leads, so she booked meetings with people who were clearly not a fit. My sales reps started pushing back. The follow-up cadence was all over the place; some leads got three emails in a week, others got one and were never touched again. And she was logging everything in a Google Sheet that nobody looked at, so we had zero pipeline visibility.

Three months in, I had spent more time fixing the process than I would have spent just doing it myself.

What a well-set-up remote appointment setter looks like in practice

After fixing everything the hard way, here is what a well-set-up remote appointment setter actually looks like in practice:

Week 1: ICP onboarding first, tools second

The first week is entirely onboarding. Not tool training, ICP training. My current appointment-setting virtual assistant listened to recorded sales calls, learned what a qualified lead sounds like versus a time-waster, and had to explain our value proposition back to me before she touched a single lead. That one step alone fixed 80% of our quality problems.

Work inside the CRM from day one

She works directly in our CRM from day one. No parallel spreadsheets, no Google Sheets, no "I'll update it later." Every lead, every touchpoint, every outcome logged in real time. If it's not in HubSpot, it didn't happen.

Fixed outreach cadence (no judgment calls)

We gave her a fixed outreach cadence, a seven-touch sequence over 14 days across email and LinkedIn, with one phone attempt on day five. She doesn't make judgment calls about when to follow up. The sequence does that for her. Consistency went up immediately. I will go as far as to say that she is the best virtual appointment setter's assistant we had.

Accountability layer: weekly pipeline review

Obviously, this consistency does not come without follow-ups. We do a 15-minute pipeline review every Monday with our sales lead. What got booked, what's in follow-up, what's dead. That's the accountability layer that makes everything else stick.

What changed in 90 days

Within 90 days, our show rate on booked calls went from 54% to 71%. Our reps stopped doing any outreach and started closing better because they were only talking to pre-qualified prospects. No lead in our CRM was older than two weeks without a logged follow-up.

Why I scaled with Wishup

We now run two appointment-setting virtual assistants, both remote, both through Wishup. I went with Wishup because their VAs come pre-trained on CRM tools like HubSpot and Salesforce. I didn't have to spend weeks on tool onboarding. That headstart saved us a full month of ramp time and meant we were generating booked calls within the first two weeks.