Head of Business Development (Building Partnerships)
Full-time · Chicago, hybrid · Pentice / Cloud9 Windy City · Reports to the CEO

1. Role and mission

Mission: You sign more profitable Class A buildings for Pentice. You find, win, and close deals with the people who control these buildings. You own each deal from the first contact to the signed agreement.

Who you sell to:

• Property management companies: They run many buildings. One relationship can open a full portfolio.

• Regional managers: They control access to many buildings in a market. They often make the first recommendation.

• Asset managers: They report to investors. They need proof that Pentice improves the return on hard-to-lease units.

• Owners: They give the final approval on many deals.

Team: Business Development. You work closely with the CEO. Operations gives you the guest proof that you use to win deals.

2. Outcomes (scorecard)

You own these results in your first 12 months. You and the CEO set the values for X, Y, Z, P, and A from the plan.

• Signed inventory

  • Sign Y new buildings or Z net new units in 12 months.

  • Each deal must meet or exceed our target contribution margin.

  • You close these deals. The CEO joins only on deals that the two of you select.

• Portfolio deals

  • Sign P agreements with property management companies or asset managers. Each agreement must open 2 or more buildings.

• Pipeline

  • Get X qualified decision-maker meetings each month by Month 6.

  • Track meetings by buyer type: property management company, regional manager, asset manager, and owner.

  • Make sure that 70% or more of meetings are about ICP buildings. ICP buildings are Class A buildings, or large units that do not perform well, in our target markets.

• Deal speed and cost

  • Decrease the median time from first meeting to signed agreement by A%.

  • Set a target cost for each signed unit, then meet that target.

• Proof for deals

  • For each signed building, capture 1 or more proof assets within 6 months. Examples are a case study, a financial result, or a testimonial. Use each asset in 3 or more active deals.

You will report these weekly KPIs: new contacts, first meetings, proposals sent, deals in negotiation, and contracts signed.

3. Key responsibilities

• Build the target list. Map the Class A buildings in our markets. For each building, find the property management company, the regional manager, the asset manager, and the owner.

• Open doors. Contact decision-makers directly. Use your network, referrals, LinkedIn, email, phone, and industry events.

• Run the full sale. Lead discovery calls, building tours, proposals, and negotiations. Close the agreement.

• Sell to each buyer differently. Give regional managers an easy yes. Give asset managers the financial case. Give owners confidence.

• Win portfolios. Turn one signed building with a management company into more buildings with that company.

• Use guest proof to sell. Work with operations to collect reviews, case studies, and financial results. Use them in every deal.

• Keep the CRM accurate. Record every contact, stage, and next step. Run a weekly pipeline review with the CEO. For each deal, show the current stage, the next action, and your requests.

• Feed the business. Tell the CEO and operations what buyers ask for and why deals stall or fail.

4. Requirements (must have)

Experience

• 6 or more years in business development, sales, or partnerships.

• 3 or more years selling to multifamily or commercial real estate decision-makers. Examples are property management companies, asset managers, REITs, or building owners.

• Experience with long B2B sales cycles that have many people in each decision.

• You closed several six-figure or multi-year agreements with many stakeholders. Single-call deals are not sufficient.

Proof of closing

• You closed deals yourself. Supporting a sales team is not sufficient.

• You can show numbers: deals closed, contract value or units signed, and time to close.

Network

• Relationships with multifamily decision-makers in Chicago or a similar US market are a strong plus. If you do not have them, you must show that you built them from zero in a new territory before.

Skills

• You can build a financial case that an asset manager accepts.

• You can lead a negotiation from first offer to signed agreement.

• You use a CRM every day and keep it accurate.

Logistics

• This is a full-time job.

• You live in Chicago or you can move there.

• You must meet buyers in person and tour buildings on a regular schedule.

5. Traits and behaviors

• You are a closer. You ask for the signature.

• You see the building decision-maker as the main customer. You see the guest as the proof.

• You build trust over months. You follow up without a reminder.

• You work from a scoreboard. You know your pipeline numbers each week.

• You are comfortable with direct feedback and direct answers.

• You bring options with clear tradeoffs, not only problems.

• You write clearly and simply. You do not use buzzwords.

• You are hands-on. You do the work yourself. You do not need a large team.

6. Structure and reporting

• Type: Full-time, exempt.

• Reports to: CEO.

• Location: Chicago, hybrid. You spend most weeks in the field with buyers and at buildings.

• Budget: You get a separate budget for events, travel, sales tools, and sales materials. You set it with the CEO.

• Support: A small team helps you with deck design, data pulls, and light marketing assets. You own the strategy, the targeting, and every sales conversation.

7. Path and promise

• You can become VP Business Development as we grow into new markets. To get this role, you must meet your targets for 2 or more quarters in a row.

• You build the business development playbook for a hospitality brand that leads its category.

• You take over deal closing from the CEO. Your work connects directly to signed buildings and the value of the company.

8. How to apply

Apply with the form below. Include:

• Your CV or LinkedIn profile.

• 3 to 5 deals that you closed yourself. For each deal, tell us: the buyer type, the deal size in units or contract value, and the time from first meeting to signature.

• A short list of the types of companies and roles in your network. For example: property management companies, regional managers, asset managers, or owners. You do not need to give names.

We will invite the best candidates to a live conversation with the CEO.

Why Pentice

If you want to own a number, move fast, and build with AI instead of around it, this is the place. Small team, real leverage, high standards, and the people who build the systems get to run them as we scale city by city. If you want a comfortable seat where effort counts more than outcomes, we are not it.

Equal opportunity

Pentice and its operating entities do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.