Repositioning a Restaurant Tech Brand for Scale, Clarity, and Category Leadership
A full-scale rebrand that clarified Checkmate’s value, elevated its presence, and reignited momentum across marketing, product, and sales surfaces.
Touchpoints
Head of Visual Design, responsible for brand development, creative direction, and cross-functional creative leadership across key brand and go-to-market surfaces.
Led brand and design functions from high-level strategy through execution.
Mentored a growing design team, supporting individual growth and raising the overall bar for creative quality.
Directed creative decisions across campaigns, the website, sales materials, and product-adjacent surfaces.
Spearheaded department-wide workflow restructuring to improve execution and collaboration.
Impact
Led a full-scale brand and go-to-market transformation that elevated positioning and drove measurable pipeline growth.
Increased internal alignment and creative confidence through systems that scaled clarity and execution.
Modernized the website to reflect strategic positioning, improve user flow, and convert high-value traffic.
Built and launched a scalable design system adopted across marketing, product, and internal teams.
Established new creative workflows to improve consistency, speed, and cross-functional visibility.
Challenges
Checkmate struggled to stand out in a crowded market. Internally, fragmented systems and outdated workflows slowed execution and weakened brand consistency.
Lack of a centralized design system led to duplicated work and inconsistent execution.
Outdated website with poor UX, unclear messaging, and low conversion.
Unstructured intake and review slowed team velocity and created friction across functions.
Strategic Initiatives
From redefining brand strategy to overhauling operations and execution, these initiatives collectively repositioned Checkmate for long-term growth and team-wide momentum.
01
Rebuilding Brand Strategy from the Inside Out
Redefined Checkmate’s brand positioning to align teams, clarify value, and lay the foundation for scalable growth.
Crafted a differentiated brand narrative that resonated with both operators and enterprise buyers.
Clarified the brand’s core value propositions and messaging pillars to strengthen go-to-market execution.
Translated complex product capabilities into simple, compelling positioning.
Built internal confidence in brand direction through structured workshops, strategy docs, and messaging guides.
Aligned marketing, product, and leadership teams around a shared strategic framework.
02
Building Scalable Design Systems
Created a unified design system to improve consistency, speed, and creative autonomy across marketing and brand surfaces.
Audited design patterns and assets to identify friction points and visual inconsistencies.
Defined core brand voice principles to guide visual and written cohesion.
Built a modular component library and scalable visual language for marketing applications.
Established clear usage guidelines to support distributed teams and agency partners.
Improved creative velocity by reducing duplicative work and enabling faster iteration.
Positioned the system as a strategic brand tool supporting execution at scale.
03
Building a High-Performing Design Team
Built a culture of clarity, trust, and ownership to elevate individual growth and team performance.
Mentored junior and senior designers through 1:1s, creative reviews, and live project coaching.
Developed personalized growth plans tailored to each designer’s strengths and goals.
Modeled strategic thinking and decision-making frameworks to improve problem-solving and autonomy.
Fostered psychological safety and a culture of curiosity, trust, and open critique.
Created scalable QA and feedback systems to ensure consistency and elevate creative standards.
Enabled designers to take ownership of major initiatives by expanding scope and accountability.
Increased visibility and alignment through shared systems, async updates, and cross-functional reviews.
Jenna is the kind of leader every designer hopes to work with: empathetic, visionary, and fully invested in her team’s growth. I had the privilege of working alongside her at Checkmate as she led a pivotal rebrand that elevated both our brand and our team. Her ability to zoom out strategically while still refining the smallest details set a new bar for what great creative leadership looks like.
Jenna cultivated a design culture grounded in clarity, autonomy, and curiosity. As a mentor, she created a safe space for honest feedback, encouraged exploration, and helped me grow into a more confident, strategic designer. Her blend of creative vision, thoughtful guidance, and deep brand expertise left a lasting impact on my career and on how I show up as a designer today.
Vong Hang
Brand Designer
04
Evolving the Website to Reflect Market Position
Modernized site structure, messaging, and UX to align with buyer expectations and improve conversion.
Restructured site architecture to reflect enterprise sales flows and reduce friction for key audiences.
Collaborated with product marketing and communications to sharpen storytelling and messaging hierarchy.
Refreshed visual design and brand voice across digital and print touchpoints.
Optimized high-traffic pages and CTAs to improve engagement and conversion.
Laid the foundation for future experimentation through clearer UX logic and scalable page patterns.
05
Restructuring Departmental Workflows
Redesigned creative and marketing workflows to increase visibility, reduce friction, and scale execution.
Standardized intake, planning, and feedback processes to streamline execution and reduce bottlenecks.
Built lightweight systems to align priorities across marketing, sales, product, and leadership.
Shifted the team from reactive production to proactive campaign planning.
Empowered designers and marketers to own their workstreams with minimal oversight.
Increased collaboration and accountability through shared tools, transparent timelines, and async rituals.
monthly transactions
restaurants
locations
increase in paid leads
growth in organic traffic-driven leads
more CTA clicks
more research downloads
increase in paid conversion rate
increase in email click-through rate
From System to Every Surface
This phase focused on building a system that could scale visually, strategically, and operationally. Every element reinforced the new positioning while addressing real-world challenges across teams and channels. From early sketches to rollout kits, brand guidelines, and swag, the work balanced polish with practicality. The goal was to ensure the brand showed up with equal strength on a keynote stage, in an investor deck, on a t-shirt, or across at a tradeshow.
Brandmark Construction
The Checkmate brand mark represents the critical link that ensures orders are fulfilled accurately, service is delivered seamlessly, and management operates with informed precision.
It symbolizes the interconnectedness of service, operations, and customer satisfaction. The checkmark in the negative space is a nod to the reliability and trust that Checkmate brings to every table, kitchen, and administrative process, marking every transaction and operation with a sign of excellence and quality assurance.
Central Themes
Connection
Reliability
Excellence
Symbolism
Checkmarks
Roman C
Roman M
Heart
Handshake
I gave the brand a clear point of view. And the tools to express it.
