To get HOA contracts, start with the management companies, not the boards. A community manager handles 10 to 40 associations, writes the bid request, and recommends a vendor the board votes on. Put one manager's name on a list, send a bid package that a volunteer board can compare in five minutes, and contact them 60 to 90 days before the current contract ends. The rest of this page is a checklist you can run through for each community.

HOAs buy landscaping, pool care, paving and seal coating, painting, roofing, tree work, pest control and snow removal. The buyers are volunteers with day jobs who meet once a month. That changes how you sell: they want a bid that is easy to compare, references from neighbors and no surprises in the budget.

List checks: managers first, boards second

Work from a list of names, not from a drive-through of neighborhoods.

  • Find the community management companies within 30 miles. Search "HOA management" plus your city, and check the county's recorded associations for the management company on each.
  • For each company, get the portfolio manager's name. The person who answers bids is usually titled community manager or portfolio manager, not the owner.
  • Add self-managed associations only after the managers. Their contact is the board president or treasurer, listed on the state's annual filing in many states.
  • Note how many communities each manager runs. A manager with 25 associations is worth ten times a single board.
  • Record each community's size (homes, acres of common area) and which service you want to bid.

A list of 30 managers and 20 self-managed boards is plenty for a first quarter.

Bid-package checks: what boards need to see

A volunteer board reads three bids and picks one. Make yours the easiest to compare. A good package is three to four pages:

  • Scope in plain lines: "Mow and edge weekly April through October, biweekly otherwise. Blow off hard surfaces every visit. Trim shrubs twice a year."
  • One monthly price and an annual total, with extras priced separately (mulch per yard, aeration per acre, a per-hour rate for extra work).
  • A certificate of insurance and your license number, attached, not "available on request".
  • Three references from other associations, with the manager's name and number.
  • A start date, contract length (one year with a 30 or 60 day exit is the easiest to approve) and what happens at renewal.

A worked example: Tamsin's crew mows a 120-home community. Her bid is $2,100 a month for 12 months, $25,200 a year, with a note that mulch for the entrance beds is $62 a yard installed. The board sees one number, one list of extras and no hidden fee. That is a better position than a lower bid with a line that reads "additional services as needed".

Meeting checks: the board calendar

Boards decide at meetings, and most meet monthly. Ask the manager for three dates: when the next board meeting is, when the bid deadline is, and when the current contract ends. Work backward.

  • Contract ends June 30. The board wants to vote in May. Bids are due in April. Your first note should land in February or early March.
  • Many associations set their budget for the next year between September and November. Landscaping and paving costs have to be in that budget, so a September note beats a January one.
  • Ask whether vendors present in person. Some boards want ten minutes at the meeting; others vote on the manager's summary.

If the manager says the contract was just renewed for three years, ask for the renewal month and put it in your calendar. You will not win that one this year, but you can be the first call in two years.

Message checks: the note to the community manager

Keep it short and specific to the manager's portfolio.

Subject: Landscaping bid for your communities in Cedar Ridge

Hi Denise, I run a six-person landscaping crew in the county and we already maintain two associations near your Cedar Ridge portfolio. When does the current grounds contract end for Oakfield Commons? I would like to send a bid before your board's budget meeting. I can walk the property this week and have a written bid to you in two business days. Three references from other associations are attached.

It asks one question the manager can answer in a line, offers a free site walk and a deadline, and makes the next step easy. Include your physical business address and a plain way to opt out if you send this by email in bulk, as the CAN-SPAM rules require.

Follow-up checks: before the vote

  • Day 3 to 4: if there is no reply, send one line asking whom to send the bid to.
  • After the walk: send the bid within 48 hours.
  • One week before the vote: ask the manager if the board has questions you can answer in writing.
  • After the vote, win or lose: ask the manager what decided it, and when the next bid cycle opens. A manager who passed on you this year will often tell you why.

Our guide on following up on a quote covers the wording if you want more options. For the buyer's side of the work, how to cold email property managers uses the same approach.

Renewal checks: 90 days before the term ends

Once you win one, the renewal is the real prize. Put a reminder in your calendar 120 days before the term ends. At 90 days, send the manager a one-page summary: visits made, extras done, anything the board asked for and what you did. Offer to renew at the same rate or explain a small change before the budget is set, not after. Managers don't like surprises in an invoice, and boards don't like them in a budget.

Then ask for the other communities. A manager who is happy with one association is the shortest route to the next three.

Mistakes that lose HOA bids

The usual mistakes: bidding to a board without knowing when it votes; leaving out insurance; bidding low on mowing and making it back on extras (the board notices in month three); going around the manager to a board member, which burns the relationship that feeds you ten communities.

Also read the local rules: some states require associations to take multiple bids above a dollar amount, and some have open-meeting rules about how bids are opened. This is general information, not legal advice. Ask the manager what the association's process is. When you do win, put the scope, price and exit terms in writing with a plain service agreement.

If you also work for commercial owners, commercial landscaping contracts follow a similar list-and-bid approach with different timing, and commercial painting contracts shows a 45-day plan for repaint work with managers.

Finding 30 managers by name and writing to each of them is the part that takes the time. Rocketship finds the buyers, 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. There is a page on Rocketship for property management work.