Head of Business Development (Building Partnerships)

Pentice•Chicago, IL

3d•Hybrid

About The Position

The Head of Business Development owns the process of signing profitable Class A buildings for Pentice, from first contact through signed agreement. The role sells to property management companies, regional managers, asset managers, and owners, and works closely with the CEO. Operations provides guest-related proof to support sales. The position is based in Chicago with a hybrid arrangement and regular in-person buyer meetings and building tours; most weeks are spent in the field. In the first 12 months, the role is accountable for targets set with the CEO for new buildings or units signed, portfolio agreements, qualified decision-maker meetings, deal speed, and cost per signed unit. Deals must meet or exceed the target contribution margin. For each signed building, the role must help capture at least one proof asset within six months and use each asset in at least three active deals. Weekly reporting covers new contacts, first meetings, proposals, deals in negotiation, and contracts signed. The role builds the target list, maps relevant buildings and decision-makers, opens relationships, leads the full sales process, and develops portfolio opportunities. It maintains accurate CRM records and conducts weekly pipeline reviews with the CEO. It also shares buyer feedback and reasons deals stall or fail with the CEO and operations. The role has a separate budget for events, travel, sales tools, and materials, set with the CEO, and receives support with deck design, data pulls, and light marketing assets while owning sales strategy, targeting, and conversations. This is a full-time, exempt role reporting to the CEO. The position may grow into VP Business Development as the company enters new markets, subject to meeting targets for at least two consecutive quarters. The role builds the business development playbook and takes over deal closing from the CEO.

Requirements

At least 6 years of experience in business development, sales, or partnerships.
At least 3 years of experience selling to multifamily or commercial real estate decision-makers, such as property management companies, asset managers, REITs, or building owners.
Experience with long B2B sales cycles involving multiple stakeholders.
Personally closed several six-figure or multi-year agreements involving multiple stakeholders; single-call deals do not qualify.
Ability to demonstrate deal results, including deals closed, contract value or units signed, and time to close.
Personally closed deals; supporting a sales team without closing deals is insufficient.
Ability to build a financial case accepted by an asset manager.
Ability to lead negotiations from first offer through signed agreement.
Daily CRM use and accurate recordkeeping.
Live in Chicago or be able to move there.
Availability to meet buyers in person and tour buildings regularly.
Full-time availability.

Nice To Haves

Relationships with multifamily decision-makers in Chicago or a similar U.S. market.
If the candidate lacks an existing network, evidence of having built one from zero in a new territory.

Responsibilities

Build a target list and map Class A buildings in target markets, identifying property management companies, regional managers, asset managers, and owners.
Contact decision-makers through networks, referrals, LinkedIn, email, phone, and industry events.
Lead the full sales process, including discovery calls, building tours, proposals, negotiations, and closing agreements.
Tailor the sales approach to regional managers, asset managers, and owners.
Develop portfolio opportunities by expanding from one signed building to additional buildings with the same management company.
Work with operations to collect reviews, case studies, and financial results, and use these proof assets in sales deals.
Maintain accurate CRM records of contacts, deal stages, and next steps.
Run weekly pipeline reviews with the CEO, presenting each deal’s stage, next action, and requests.
Report weekly KPIs, including new contacts, first meetings, proposals sent, deals in negotiation, and contracts signed.
Share buyer requests and reasons deals stall or fail with the CEO and operations.
Set the sales budget for events, travel, sales tools, and sales materials with the CEO.
Meet buyers in person and tour buildings on a regular schedule.