Marketing Manager (Proof & Sales Enablement)

Pentice•Chicago, IL

1d•Hybrid

About The Position

The Marketing Manager (Proof & Sales Enablement) helps Pentice sign more Class A buildings by equipping the Head of Business Development with credible proof, buyer-specific sales materials, and warm introductions to target accounts. The role does not close deals. It works daily with the Head of Business Development and partners with operations to collect guest and building results that can demonstrate value to prospective buyers, including property management companies, regional managers, asset managers, and building owners. The role owns first-year outcomes including creating at least one qualifying proof asset for each signed building within six months; sourcing a monthly target of first meetings with named decision-makers at target accounts; maintaining current decks, one-pagers, and case studies for each buyer type; and improving direct and repeat bookings and guest reviews. The meeting target (X), booking-share target (B), and minimum average-rating target (R) are to be set with the Head of Business Development. Weekly reporting covers proof assets shipped, marketing-sourced meetings, target accounts touched, and new reviews. The manager builds proof assets from reviews, photos, guest stories, and financial results; creates buyer-specific sales materials; runs targeted account outreach, events, and guest-side marketing; maintains brand materials; and reports progress in a weekly pipeline review. This is a full-time, exempt position based in Chicago with a hybrid arrangement and regular in-person work at buildings, tours, and events. The role reports to the CEO and has a budget for design tools, photo and video, targeted ads, and events, set with the CEO. The role opens after the Head of Business Development is in place. The position offers a potential path to Head of Marketing as the company expands into new markets, contingent on meeting targets for at least two consecutive quarters.

Requirements

3 to 5 years of experience in B2B marketing, sales enablement, or product marketing.
Experience supporting a sales team in a long sales process with multiple decision-makers.
Ability to provide case studies, decks, or campaigns personally created, along with measurable results such as meetings sourced, deals supported by materials, or conversion changes.
Clear, simple copywriting skills.
Ability to design decks and one-pagers using tools such as Canva, Figma, or Google Slides.
Ability to run email and LinkedIn campaigns targeting named accounts.
Ability to retrieve and report metrics from CRM and analytics tools.
Must live in Chicago or be able to move there.
Must be able to attend buildings, tours, and events in person on a regular schedule.
Must be comfortable with direct feedback, working hands-on, creating assets personally, and moving quickly.

Nice To Haves

Experience in real estate, multifamily, hospitality, or B2B services is a strong plus.

Responsibilities

Collect reviews, photos, guest stories, and financial results from each building in coordination with operations.
Turn collected evidence into case studies and one-page building summaries that meet the Proof Checklist: recent, specific, quantified, and representative of a building like the prospective buyer’s building.
Create and maintain current decks, one-pagers, and case studies for property management companies, regional managers, asset managers, and owners.
Develop buyer-specific sales narratives, including low-risk messaging for regional managers, financial results and comparisons for asset managers, and brand-quality and trust evidence for owners.
Run email, LinkedIn content, and targeted advertising to named people at target accounts selected by the Head of Business Development.
Plan building tours, small owner dinners, and Pentice’s presence at Chicago real estate events.
Grow direct and repeat bookings through email, the website, and review requests, using positive reviews as proof for sales efforts.
Maintain the website, sales decks, and in-unit materials to keep the brand consistent.
Join the weekly pipeline review and report shipped assets, sourced meetings, and what the Head of Business Development needs next.
Report weekly KPIs: proof assets shipped, marketing-sourced meetings, target accounts touched, and new reviews.