An HR director at a 100-person company is rarely short on vendors. They are short on timing. Write to them in the month they are planning that project and you get a reply. Write in the month they are in the middle of open enrollment and you get silence, however good the product.

HR buys many things: benefits administration, payroll add-ons, background checks, recruiting tools, training, employee assistance programs, engagement surveys, compliance software. What they buy, how much they can sign for, and when they look are all more predictable than most vendors think. This guide gives you the calendar, the approval path and a pilot offer.

What HR buys and what it passes to finance

At a company with 30 to 300 employees, the HR director or people-operations lead often has a budget of their own and a spend limit above which the CFO or owner signs. The limit is different everywhere, but a common pattern is that small recurring tools and one-off training sit under it and anything that is a multi-year contract or touches payroll goes up. So you have two readers: the HR lead who wants it, and the person above who funds it. Write the first email for the first, and give the HR lead material they can pass to the second.

The HR lead's risk is simple: if your product fails, employees complain, and it lands on HR. So they respond to a small first step with a clear end date, not to a three-year commitment.

The HR calendar: which month to write for what

This is a typical year for a company on a calendar fiscal year. Check each company's own cycle, but use this as the default.

  • January and February. New-year compliance: tax forms, ACA reporting prep, policy updates. Good for compliance tools, payroll services, handbook rewrites.
  • February to April. Annual reviews and merit cycles. Good for performance-management tools and manager training. Mid-year budgets for July fiscal-year companies are drafted in this window.
  • May to July. Benefits renewals start getting shopped. Brokers and carriers quote on schedules that begin months before the plan year. A benefits-related vendor that writes in September is already late.
  • June to August. Summer hiring waves, intern programs, onboarding refreshes. Recruiting tools and background checks are timely.
  • September to November. Open enrollment for many employers, and next-year budget drafts. HR is stretched thin: write for December or January starts, and keep emails short.
  • December. Year-end. Budget approvals, and the "use it or lose it" spending some departments do. Offer a January start.

That calendar also tells you when not to call. A message that asks for a meeting during open enrollment competes with every benefits question employees have. The same message in January lands on a calmer desk. For general timing, see the best day and time to send.

Finding HR leads at 30 to 300 person companies

Titles to look for: HR Director, HR Manager, Head of People, People Operations Manager, Director of Talent. At the small end the title may be Office Manager or Controller. A company that posts several job openings has a hiring HR team. A company with turnover visible on job boards or reviews often has a retention problem you can speak to.

Company sites, LinkedIn pages and local business journals will give you names; this guide covers confirming the right person. Group your list by cycle: "hiring in Q4," "benefits renewal in Q1." Each group gets a different email.

A first email to an HR manager

Subject: Manager training before your January review cycle

Hi Tasha, I saw that you posted two supervisor roles this month. New managers often get their first set of direct reports right before performance reviews, which is a rough week. I run a 90-minute session on giving a first review without a lot of conflict, with a one-page script for each manager. I'd like to run it with one team as a 30-day pilot, so you can see what the managers say before deciding anything more. Cost is $900 for the session. Aaron Whitfield, [mailing address]. Reply "no" and I'll stop.

The email names a trigger, offers one piece with a price, and frames it as a pilot. It also gives her something to show her own boss: a limited cost for a defined group.

Writing for the CFO who signs next

When an HR lead says yes, they still need approval. Make that step easy by sending a single page they can forward. It should say what the pilot is, who is in it, what it costs, how you will measure the result (a short manager survey, completion, or time saved), and what the next step would cost. If the HR lead can attach this to an email to the CFO, you've done half their selling for them. The structure in writing for the budget owner shows what finance wants to see.

Following up around enrollment season

If your first email lands in October and goes unanswered, don't chase. Send a short note in the first week of November: "Not asking for time during enrollment. I'll check back on December 2 about a January start." Then do exactly that. HR people notice a vendor who respects their calendar, and they remember it when the pressure is off.

If you sell a consulting-style service, the HR consulting guide goes further on that side.

Turning a pilot into a contract

At the end of the 30 days, schedule a 20-minute review with the HR lead, ideally with the person who signs. Bring three things: what you did, what the participants said in their own words, and a proposal for the next three or six months at a stated price. Ask for the decision in the room or a date for it. A pilot with no end date turns into free work.

The hardest part is the calendar: knowing which of 100 HR leads to write to this month and which to hold until January. Rocketship finds HR leaders by name, emails them from your own Gmail, follows up, and books the meeting on its own. Plans that get you customers start at $24.99 a month (Launch), and both Launch and Frontier start with a 7-day free trial, card required. See how the AI workers run it.