Marketing Manager - Proof & Sales Enablement

Marketing Manager (Proof & Sales Enablement)
Full-time · Chicago, hybrid · Pentice / Cloud9 Windy City · Reports to the CEO

1. Role and mission

Mission: You help Pentice sign more Class A buildings. You do not close deals. You give the Head of Business Development 3 things: proof that wins trust, materials for each buyer, and warm doors at target accounts.

Team: Marketing. You work with the Head of Business Development each day. You work with operations to collect guest proof.

Who our buyers are: Property management companies, regional managers, asset managers, and owners of Class A buildings. Guests are not the main customer. Guest results are the proof that wins buildings.

2. Outcomes (scorecard)

You own these results in your first 12 months. You and the Head of Business Development set the values for X, B, and R.

1. Proof density

   • For each signed building, ship 1 or more proof assets within 6 months.

   • Each asset must pass the Proof Checklist: it is recent, specific, quantified, and it shows a building like the buyer's building.

   • Generic brand content does not count.

2. Marketing-sourced meetings

   • Source X first meetings each month.

   • A meeting counts only if it is a first meeting with a named decision-maker from the target account list, and it is logged in the CRM.

   • Form fills, followers, and general leads do not count.

3. Sales materials

   • Keep a current deck, one-pager, and case study set for each buyer type: property management company, regional manager, asset manager, and owner.

   • The Head of Business Development must never wait on a material for an active deal.

4. Guest-side fuel

   • Increase direct and repeat booking share by B percentage points.

   • Increase review volume and keep the average rating at or above R.

You will report these weekly KPIs: proof assets shipped, marketing-sourced meetings, target accounts touched, and new reviews.

3. Key responsibilities

• Build the proof engine. Collect reviews, photos, guest stories, and financial results from each building. Work with operations to get them. Turn them into case studies and one-page building summaries.

• Make materials for each buyer. Give regional managers a simple, low-risk story. Give asset managers financial results and comparisons. Give owners proof of brand quality and trust.

• Warm up target accounts. The Head of Business Development selects the accounts. You run email, LinkedIn content, and targeted ads to named people at those accounts.

• Run events. Plan building tours, small owner dinners, and Pentice's presence at Chicago real estate events.

• Grow the guest side. Grow direct and repeat bookings with email, the website, and review requests. Every good review becomes proof for the next deal.

• Keep the brand consistent. Maintain the website, the decks, and in-unit materials.

• Report each week. Join the weekly pipeline review. Show what you shipped, which meetings you sourced, and what the Head of Business Development needs next.

4. Requirements (must have)

Experience

• 3 to 5 years in B2B marketing, sales enablement, or product marketing.

• Experience supporting a sales team in a long sale with many decision-makers.

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

Proof of results

• You can show case studies, decks, or campaigns that you made yourself.

• You can show numbers: meetings sourced, deals that your materials supported, or conversion changes.

Skills

• You write clear, simple copy.

• You can design decks and one-pagers in tools such as Canva, Figma, or Google Slides.

• You can run email and LinkedIn campaigns aimed at named accounts.

• You can get your own numbers from the CRM and analytics tools.

Logistics

• This is a full-time job.

• You live in Chicago or you can move there.

• You must go to buildings, tours, and events in person.

5. Traits and behaviors

• You serve the sale. You measure your work by meetings and signed buildings, not by awareness.

• You chase proof. You ask for numbers, photos, and quotes until you have them.

• You ship fast. A good case study this week is better than a perfect one next month.

• You are comfortable with direct feedback and direct answers.

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

• You are hands-on. You make the assets yourself.

6. Structure and reporting

• Type: Full-time, exempt.

• Reports to: CEO. You work each day with the Head of Business Development.

• Location: Chicago, hybrid. You must work in person on a regular schedule.

• Budget: You get a budget for design tools, photo and video, targeted ads, and events. You set it with the CEO.

• Start date: We open this role after the Head of Business Development is in place. Until then, freelancers do this work.

7. Path and promise

• You can grow into Head of Marketing as we expand into new markets. To get this role, you must meet your targets for 2 or more quarters in a row.

• You build the proof system for a hospitality brand that leads its category.

• You can see how each asset that you ship helps to sign a building.

8. How to apply

Apply with the form below. Include:

1. Your CV or LinkedIn profile.

2. 2 or 3 case studies, decks, or one-pagers that you made for a sales team. Send links or PDFs.

3. 3 to 5 bullets about results that you owned. Tell us what changed, by how much, and in how much time. Examples are meetings sourced or deals that your materials supported.

We will invite the best candidates to a live conversation with the CEO and the Head of Business Development.

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.