Lead Designer, Pointe Grand

📍 Job Overview

Job Title: Lead Designer, Pointe Grand

Company: Hillpointe

Location: Winter Park, FL

Job Type: Full-Time

Category: Creative & Media / Art & Design / Marketing

Date Posted: 2026-07-28T21:13:15

Experience Level: 5-10 years

Remote Status: On-site

🚀 Role Summary

• Serve as the primary content creator and visual identity steward for the Pointe Grand Communities brand, driving brand consistency across a growing portfolio.

• Develop and deploy a comprehensive range of visual assets, including property signage, large-format advertising, print collateral, and digital marketing materials.

• Maintain and enforce brand guidelines, ensuring all creative output aligns with the Pointe Grand brand standards under the direction of leadership.

• Integrate AI-powered design tools into the creative pipeline to accelerate ideation, asset generation, and production efficiency while upholding brand integrity.

📝 Enhancement Note: This role is positioned as a critical individual contributor with a clear path for future leadership growth, indicating a need for strong foundational design skills, brand stewardship, and a proactive approach to integrating new technologies like AI into design workflows. The emphasis on "content-creator-first" and "individual contributor today with the potential to grow and lead a design team over time" suggests a focus on hands-on execution and a future vision for team building.

📈 Primary Responsibilities

• Design and produce a wide array of Pointe Grand brand assets, including property signage (monument, wayfinding, leasing office, amenity), large-format advertising (billboards, bandit signs, banners), print collateral (flyers, brochures, leasing materials, welcome packets), and digital assets (social templates, digital ads, email and web graphics).

• Lead new design initiatives from conceptualization through to final file preparation, ensuring all deliverables meet project specifications and brand standards in a high-volume, fast-paced environment.

• Prepare and package print-ready files with meticulous attention to detail regarding accurate dimensions, bleeds, color profiles, and export settings for vendor handoff.

• Actively maintain and update the Pointe Grand brand guidelines, serving as the subject matter expert to ensure creative consistency across all visual mediums, including digital, print, presentations, and signage.

• Create mid-level motion graphics for animated social content, digital advertisements, and simple promotional videos using After Effects or equivalent software, collaborating with the Creative Production Director to integrate static and motion design into unified campaigns.

• Leverage AI tools within the design pipeline for asset generation (imagery, backgrounds, textures, mockups), production acceleration (resizing, background removal, upscaling, variations), rapid ideation, and AI-assisted motion/video elements, ensuring all AI-generated outputs remain on-brand and production-accurate.

• Develop and maintain Canva templates to empower property, marketing, and operations teams for self-service of on-brand assets, fostering a collaborative production environment.

• Partner closely with the Creative Production Director to amplify output by combining static design with motion graphics and video, and by building scalable templates and systems for wider team and vendor deployment.

• Collaborate with Property Marketing and Property Operations teams to understand and deliver specific asset needs for each property, ensuring alignment with strategic goals.

• Review and manage the work of external agencies and vendors as required, ensuring quality and adherence to brand standards.

📝 Enhancement Note: The responsibilities highlight a dual focus on hands-on design execution and strategic brand stewardship. The inclusion of AI-powered design and Canva template creation indicates a forward-thinking approach to design operations and scalability. The emphasis on collaboration with various internal teams and external vendors suggests the need for strong communication and project management skills alongside design expertise.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Graphic Design, Fine Arts, Communications, or a related field is typically expected for roles of this caliber. Equivalent professional experience and a strong portfolio can often substitute for formal education.

Experience: 5+ years of professional design experience, with a significant portion focused on brand identity development, production work, and content creation for marketing purposes. Experience within the multifamily or real estate industry is strongly preferred, demonstrating an understanding of sector-specific design needs and market dynamics.

Required Skills:

• Expert proficiency in Adobe Illustrator and Adobe Photoshop for detailed graphic design and image manipulation.

• Comfortable and proficient in Canva for template creation and collaborative production workflows.

• Mid-level motion graphics capability, specifically in After Effects or equivalent software, for creating animated content.

• Demonstrated comfort and practical experience using AI tools as an integral part of the design pipeline for asset generation and production acceleration.

• Strong understanding of brand management principles, visual design systems, and the ability to maintain brand consistency across diverse media.

• Meticulous attention to detail and a proven track record of production accuracy for both print and digital assets.

• Excellent visual design skills, including typography, color theory, layout, and composition.

• Strong project management abilities to handle multiple concurrent priorities in a fast-paced environment. Preferred Skills:

• Experience within the multifamily, real estate, or related industries, providing context for property marketing and development visuals.

• Familiarity with project management software for tracking design tasks and vendor timelines.

• Understanding of vendor production processes, including pre-press requirements and large-format printing.

• Experience in developing and managing design systems or style guides.

• A portfolio showcasing a breadth of creative work, including branding, signage, digital assets, and motion graphics.

📝 Enhancement Note: The qualifications emphasize advanced technical skills in core design software, coupled with a modern skillset in AI and collaborative tools like Canva. The preference for industry experience and the explicit mention of a portfolio suggest that practical application and demonstrable results are highly valued. The combination of expert-level design and mid-level motion graphics indicates a versatile creative professional.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio demonstrating a strong command of graphic design principles, brand identity development, and visual systems.

• Showcase a range of projects including property signage (exterior and interior), large-format advertising, print collateral (brochures, flyers), and digital assets (social media graphics, web banners).

• Include examples of motion graphics projects (animated social posts, short promotional clips) created in After Effects or similar software.

• Present case studies or examples that highlight the effective use of AI tools within the design process, demonstrating how AI accelerated ideation, asset creation, or production.

• Feature examples of Canva templates designed for user-friendly self-service by non-design teams.

• Demonstrate a clear understanding of production accuracy for print and digital deliverables, with examples of print-ready files or high-resolution digital assets. Process Documentation:

• Provide examples of how you have maintained and enforced brand guidelines, perhaps through style guides or workflow documentation for ensuring consistency.

• Illustrate your process for taking a design project from initial concept and brief through to final asset delivery, including client/stakeholder feedback loops.

• Showcase how you prepare files for external vendors, detailing your approach to ensuring accuracy and efficient production.

• If applicable, include examples of how you've built scalable design systems or templates that enable broader team or vendor adoption.

📝 Enhancement Note: The portfolio requirements are heavily geared towards demonstrating practical application of design skills, brand stewardship, and proficiency with modern tools including AI and Canva. The emphasis on process documentation suggests a need for candidates who can articulate their workflow and ensure consistency and efficiency in design operations.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for a Lead Designer with 5-10 years of experience in a high-cost-of-living area like Winter Park, FL, the estimated annual salary range is $75,000 - $105,000. This estimate considers the expert-level design skills, motion graphics capability, AI integration experience, and the strategic importance of the role within a growing real estate development firm.

Benefits:

• Comprehensive health, dental, and vision insurance plans.

• Generous paid time off (PTO) and company holidays.

• 401(k) retirement savings plan with company matching contributions.

• Opportunities for professional development, including training in new design software, AI tools, and industry conferences.

• Potential for performance-based bonuses or recognition programs.

• Access to cutting-edge design technology and software.

Working Hours: The standard working hours for this role are approximately 40 hours per week, reflecting a full-time commitment. While the role operates in a fast-paced environment, there may be flexibility for occasional overtime to meet project deadlines, particularly during new property launches or major campaign rollouts.

📝 Enhancement Note: The salary range is an estimation based on typical compensation for a Lead Designer role in a major metropolitan area within the US, factoring in the specified experience level and the specialized skills (AI, motion graphics, brand stewardship) required. Benefits are standard inclusions for full-time roles at companies of this nature, with a focus on professional growth relevant to the creative field.

🎯 Team & Company Context

🏢 Company Culture

Industry: Real Estate Development & Investment Management, specifically focused on workforce housing in the Sun Belt region. Hillpointe is recognized as a top builder and developer by NMHC, indicating a strong market presence and commitment to execution excellence.

Company Size: Hillpointe is a substantial organization, likely falling into the 201-500 or 501-1000 employee range, given its integrated approach and top-tier industry rankings. This size suggests a structured environment with established processes but also opportunities for impact.

Founded: Hillpointe was founded on a long and proven track record in real estate development, implying decades of experience and a stable, established foundation. This history points to a company culture that values expertise, reliability, and strategic growth.

Team Structure:

• The Lead Designer will be part of the Brand & Creative team, reporting directly to the VP, Brand & Creative.

• They will collaborate closely with the Creative Production Director, who likely oversees video and motion graphics output.

• The role involves significant cross-functional partnership with Property Marketing and Property Operations teams, requiring strong interpersonal and communication skills.

• As an individual contributor with potential for growth, the structure is currently lean, allowing for direct impact and influence. Methodology:

• Hillpointe's core methodology emphasizes in-house general contracting expertise for direct control over cost and delivery. This translates to a culture of efficiency, accountability, and hands-on problem-solving.

• The integration of AI into the design pipeline reflects a commitment to leveraging technology for innovation and accelerated execution.

• The development of scalable systems and templates (e.g., in Canva) points to a focus on process optimization and empowering broader teams.

Company Website: hillpointe.com

📝 Enhancement Note: The company's integrated operational model and focus on workforce housing suggest a culture that values efficiency, execution, and market responsiveness. The "career-defining opportunity" framing indicates an environment that encourages professional growth and rewards contribution. The emphasis on in-house capabilities points to a value placed on internal expertise and control.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a Lead Designer, signifying a mid-to-senior level position within the creative function. It requires a high degree of autonomy, expertise in core design disciplines, and the ability to manage projects from concept to completion. The "individual contributor today with the potential to grow and lead a design team over time" descriptor highlights a clear upward trajectory, moving from expert execution to team leadership and strategic oversight.

Reporting Structure: The Lead Designer reports directly to the VP, Brand & Creative. This provides a clear line of communication with senior leadership responsible for the overall brand strategy and creative direction. Close collaboration with the Creative Production Director is also a key element of the reporting structure, ensuring synergy between static design and motion/video content.

Operations Impact: The Lead Designer's impact is crucial in shaping the visual identity and market perception of the Pointe Grand Communities brand. By creating compelling and consistent assets, they directly influence property leasing rates, brand recognition, and overall market competitiveness. Their work supports sales efforts by providing high-quality marketing materials and strengthens operational efficiency through scalable design systems and templates. The integration of AI and scalable templates further amplifies their impact by enabling faster, more consistent deployment of brand assets across a growing portfolio.

Growth Opportunities:

• Team Leadership: The most direct growth path is the potential to lead and build a dedicated design team as the Pointe Grand portfolio expands. This would involve hiring, managing, and mentoring junior designers.

• Strategic Brand Development: Opportunity to take on greater strategic responsibility in shaping the long-term visual identity and brand narrative of Pointe Grand communities.

• Advanced Technology Integration: Become a pioneer in integrating emerging design technologies, including advanced AI applications and immersive design experiences, into the company's creative workflows.

• Cross-Functional Leadership: Develop expertise in collaborating with and influencing other departments (e.g., Development, Operations, Capital Markets) through impactful visual communication.

• Industry Specialization: Deepen expertise in real estate marketing design, potentially becoming a recognized specialist within the firm or the industry.

📝 Enhancement Note: The growth potential is significant, moving beyond pure execution to strategic leadership and technological innovation. The company's growth trajectory in the Sun Belt market provides a fertile ground for a designer to expand their influence and responsibilities. The emphasis on AI suggests a forward-looking company that invests in its creative talent's ability to adapt and lead in evolving technological landscapes.

🌐 Work Environment

Office Type: This role is designated as "On-site," indicating a requirement to work from the company's office location in Winter Park, FL. This fosters direct collaboration, team cohesion, and immediate access to resources.

Office Location(s): Winter Park, Florida, a vibrant city within the Orlando metropolitan area, offering a blend of professional opportunities and desirable living conditions. The specific office address would be provided upon inquiry or during the interview process.

Workspace Context:

• The work environment is described as "fast-paced" with "multiple concurrent priorities," typical of a growing company in the real estate development sector.

• As a primary creative resource, the Lead Designer will have access to necessary design software, hardware, and potentially specialized equipment.

• The collaborative nature of the role means opportunities to interact with colleagues across different departments, including marketing, operations, and production, fostering a dynamic and interconnected workspace.

• The emphasis on AI integration suggests a modern workspace that embraces technological advancements to enhance creative output.

Work Schedule: The role involves a standard 40-hour work week. While on-site presence is required, the fast-paced nature may necessitate occasional flexibility to meet critical project deadlines, especially around property launches or major marketing campaigns. This balance aims to ensure project completion while maintaining a productive work environment.

📝 Enhancement Note: The on-site requirement is a key differentiator, emphasizing a preference for in-person collaboration and team integration. The description of the workspace suggests an environment that is both demanding and supportive, encouraging innovation and efficiency within a structured real estate development context.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application, resume, and portfolio to assess foundational skills, experience alignment, and creative output.

• Portfolio Review & Technical Interview: A deeper dive into your portfolio with the VP, Brand & Creative and/or Creative Production Director. This stage will assess your design process, technical proficiency (Adobe Suite, After Effects, AI tools), brand understanding, and problem-solving capabilities. Expect to discuss specific projects, your role, and project outcomes.

• Skills Assessment/Creative Challenge: You may be asked to complete a design challenge or a brief creative exercise to evaluate your ability to translate a brief into on-brand assets, manage time effectively, and demonstrate your design thinking under pressure. This could involve creating a concept for a new property sign or a social media campaign element.

• Team/Cultural Fit Interview: An interview with key stakeholders, potentially including members of the marketing or operations teams, to gauge your collaborative style, communication skills, and alignment with Hillpointe's company culture and values.

• Final Interview: Potentially with a senior executive to discuss overall fit, career aspirations, and the strategic vision for the role.

Portfolio Review Tips:

• Curate Strategically: Select 5-7 of your strongest, most relevant projects that showcase your expertise in brand identity, print, digital, signage, and motion graphics. Prioritize projects that demonstrate your ability to work with brand guidelines and integrate AI.

• Showcase Process: For each project, clearly articulate the brief, your role, your design process (including concept development and iteration), the tools used (especially Adobe Suite, After Effects, AI), and the final outcome/impact.

• Highlight AI Integration: If possible, include projects where you explicitly used AI tools. Detail how you used them (e.g., for ideation, asset generation, mockups) and the benefits achieved (e.g., speed, new creative avenues).

• Demonstrate Production Accuracy: Include examples of print-ready files or high-resolution digital assets. Be prepared to discuss your understanding of CMYK vs. RGB, bleeds, and file formats.

• Tell a Story: Frame your portfolio not just as a collection of images, but as a narrative of your problem-solving abilities and creative impact.

Challenge Preparation:

• Deconstruct the Brief: Understand the target audience, brand context, and objective of any design challenge.

• Prioritize On-Brand Execution: Ensure your solutions strictly adhere to the Pointe Grand brand guidelines.

• Showcase Efficiency: If time is a constraint, demonstrate how you can quickly generate effective concepts and assets, perhaps leveraging AI or pre-existing templates.

• Articulate Your Decisions: Be ready to explain why you made specific design choices, linking them back to the brief and brand strategy.

📝 Enhancement Note: This section provides a structured approach to the interview process, emphasizing the importance of a well-curated portfolio that highlights modern design practices, including AI integration and scalable template creation. The advice is tailored to help candidates demonstrate not only creative talent but also operational efficiency and strategic thinking relevant to a real estate development context.

🛠 Tools & Technology Stack

Primary Tools:

• Adobe Creative Suite: Expert proficiency required in Adobe Illustrator and Adobe Photoshop for core graphic design tasks, including vector illustration, photo editing, and layout creation.

• Motion Graphics Software: Mid-level proficiency in Adobe After Effects or equivalent (e.g., Apple Motion) for creating animated social content, digital ads, and promotional videos.

• Collaborative Design Platform: Strong comfort and proficiency with Canva for template creation, collaborative production, and enabling self-service for internal teams.

• AI Design Tools: High degree of comfort and practical application with various AI-powered design tools for asset generation (imagery, backgrounds, textures, mockups), production acceleration (resizing, background removal, upscaling, variations), and rapid ideation. Examples might include Adobe Firefly, Midjourney, DALL-E, or similar generative AI platforms.

Analytics & Reporting: While not a primary focus for this design role, a basic understanding of how design assets perform within digital marketing campaigns (e.g., click-through rates on digital ads, engagement on social media) is beneficial for iterative design improvements. Familiarity with analytics dashboards used by marketing teams could be an advantage.

CRM & Automation: Not directly applicable to the core design responsibilities, but familiarity with how marketing assets are deployed within CRM systems or marketing automation platforms (e.g., email marketing tools) can provide context for asset requirements.

📝 Enhancement Note: The technology stack is heavily weighted towards design and creative production tools, with a strong emphasis on both industry-standard professional software (Adobe Suite) and modern, collaborative platforms (Canva, AI tools). This highlights the company's commitment to leveraging technology for efficiency and innovation in its creative output.

👥 Team Culture & Values

Operations Values:

• Execution Excellence: A strong emphasis on delivering high-quality work efficiently and on time, reflecting the company's integrated development and construction model. This means a focus on getting things done, accurately and effectively.

• Brand Stewardship: A deep respect for the brand's integrity and consistency. Operations professionals are expected to be guardians of the brand, ensuring all visual communications reinforce the Pointe Grand identity.

• Innovation & Adaptability: A willingness to embrace new technologies and methodologies, such as AI-powered design, to enhance creative output and operational efficiency.

• Collaboration & Partnership: A belief in the power of teamwork, both within the creative department and across other functional areas like marketing, operations, and property management.

• Data-Driven Improvement: While primarily a creative role, there's an underlying expectation to understand how visual assets contribute to business goals, implying a receptiveness to feedback and performance data for continuous improvement.

Collaboration Style:

• Cross-Functional Integration: The role requires seamless collaboration with the Creative Production Director, Property Marketing, and Property Operations teams. This involves proactive communication, understanding diverse needs, and delivering cohesive visual solutions.

• Process-Oriented Feedback: A culture that encourages constructive feedback on design work and processes to refine output and improve workflow efficiency.

• Knowledge Sharing: An environment where team members are encouraged to share best practices, new techniques (especially with AI), and insights to elevate the entire team's capabilities.

• Agile Production: The fast-paced nature of the industry necessitates an agile approach to design production, allowing for quick turnarounds and iterative development.

📝 Enhancement Note: The culture values a blend of traditional design discipline with a modern, forward-thinking approach to technology and collaboration. The emphasis on "execution excellence" and "brand stewardship" aligns with the firm's integrated real estate development model, where control and consistency are paramount.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Volume and Quality: The primary challenge will be maintaining high creative standards and brand consistency across a rapidly growing portfolio with high-volume demands for various asset types.

• Integrating AI Seamlessly: Effectively integrating AI tools into the design pipeline while ensuring brand integrity, ethical use, and production-readiness requires ongoing learning and strategic application.

• Managing Diverse Stakeholder Needs: Collaborating with various internal teams (Marketing, Operations) and external vendors, each with potentially different priorities and feedback, requires strong communication and negotiation skills.

• Staying Ahead of Design Trends: Continuously evolving design trends and technologies, especially in AI and digital media, requires a commitment to ongoing learning and adaptation.

Learning & Development Opportunities:

• AI Design Mastery: Opportunities to become a recognized expert within the company for leveraging AI in creative workflows, potentially leading workshops or developing best practices.

• Brand Strategy Input: As the Pointe Grand brand matures, there will be opportunities to contribute more significantly to its strategic visual direction and evolution.

• Team Leadership Development: The clear path to potentially leading a design team offers significant opportunities for developing management, mentorship, and strategic planning skills.

• Industry Exposure: Attending industry conferences (real estate marketing, design technology) and participating in relevant training programs to enhance skills and network.

• Cross-Functional Understanding: Gaining deeper insights into property development, marketing, and operations processes, which can inform more effective and strategic design solutions.

📝 Enhancement Note: The challenges presented are typical for a lead role in a growth-stage company, emphasizing the need for strong execution, adaptability, and strategic thinking. The growth opportunities are directly tied to the company's expansion and the evolving landscape of design technology.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for ensuring brand consistency across a large and growing portfolio of properties, especially when dealing with high-volume asset requests." (Focus on brand guidelines, template systems, and workflow management.)

• "Walk us through a project where you integrated AI tools into your design workflow. What was the challenge, how did you use AI, and what was the outcome?" (Highlight your practical experience with AI, focus on benefits like speed, ideation, or efficiency.)

• "How do you approach balancing creative vision with production constraints and vendor requirements in a fast-paced environment?" (Emphasize your understanding of print/digital production, communication with vendors, and ability to deliver practical, on-brand solutions.) Company & Culture Questions:

• "What attracts you to Hillpointe and the Pointe Grand brand specifically?" (Research Hillpointe's mission, market position, and workforce housing focus. Connect your design philosophy to their goals.)

• "How would you contribute to a culture of innovation and collaboration within our creative team and across departments?" (Discuss your proactive approach to learning new tools, sharing knowledge, and building strong working relationships.)

• "How do you measure the success of your design work, beyond aesthetic appeal?" (Discuss metrics like brand adherence, asset usability, stakeholder satisfaction, and indirectly, impact on marketing goals.) Portfolio Presentation Strategy:

• Structure for Impact: Begin with a brief overview of your design philosophy and experience. Then, present 3-4 key projects that best represent your skills for this role, focusing on diversity of asset types and complexity.

• Highlight AI and Canva: Dedicate specific slides or discussion points to projects where you utilized AI tools or created Canva templates. Clearly articulate the problem, your solution, and the quantifiable or qualitative results.

• Demonstrate Process: For each project, explain your thought process, design decisions, and how you navigated challenges. Use visuals to show early concepts, iterations, and the final deliverables.

• Quantify Results: Whenever possible, use data or metrics to showcase the impact of your work. If direct metrics are unavailable, focus on how your design facilitated specific business objectives (e.g., improved clarity of wayfinding, increased engagement on social templates).

• Engage Your Audience: Be prepared to answer questions about your work and discuss how your skills can benefit Hillpointe. Show enthusiasm for the brand and the opportunity.

📝 Enhancement Note: This preparation guide focuses on strategic questioning relevant to the role's core responsibilities: brand stewardship, AI integration, and production efficiency. The portfolio presentation strategy emphasizes showcasing practical application, measurable results, and alignment with the company's operational values.

📌 Application Steps

To apply for this Lead Designer position:

• Submit your application through the provided link on the Greenhouse platform.

• Customize Your Resume: Tailor your resume to highlight keywords and responsibilities mentioned in this job description, such as "graphic design," "brand identity," "Adobe Illustrator," "After Effects," "AI-enabled design," "print production," and "Canva." Quantify your achievements with specific numbers where possible (e.g., "Designed 50+ property signage packages," "Developed 100+ Canva templates").

• Prepare Your Portfolio: Ensure your portfolio is up-to-date, easily accessible (e.g., via a link), and showcases your strongest work relevant to brand identity, print collateral, digital assets, signage, and motion graphics. Specifically, include examples demonstrating your use of AI tools and your ability to create scalable templates.

• Practice Your Presentation: Rehearse presenting your portfolio, focusing on clearly articulating your design process, the impact of your work, and your experience with the required tools and technologies. Be ready to discuss your approach to brand consistency and AI integration.

• Research Hillpointe: Familiarize yourself with Hillpointe's mission, their focus on workforce housing, and the Pointe Grand brand. Understand their market position and any recent projects or news to demonstrate genuine interest and alignment with their business goals.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.