Chesterton Hills works alongside organizations on their most consequential decisions and the execution that follows. We cover the full range of functions a business needs, and we stay involved through the work.
Drawn from careers across firms, industries, and geographies.
$1.5B+
In partnerships negotiated
30+
Countries entered
20+
Products & services launched
10M+
New customers acquired
Advice without implementation is just an expensive opinion.
Most firms hand over a document and move on. We stay engaged through execution and measure our contribution by what actually changed, not what was delivered.
What We Do
Areas of practice
We work across every function a business requires, from strategy and technology to marketing, finance, and operations.
Chesterton Hills was built on an observation that should be obvious but apparently is not: telling someone what to do and helping them do it are two entirely different services. Most firms only offer the first. We offer both.
The problems that reach us have usually survived a first attempt at solving them. We approach each one without assuming we already know the answer.
The presenting problem is often not the actual problem. We take the time to find out which is which before we recommend anything.
We do not apply the same framework to every situation. The situation determines the approach.
Execution is part of the work, not someone else's problem after we finish.
We work to leave every client with greater clarity, capability, and momentum than when we started.
How We Work
A consistent approach to every engagement
01
Discovery
We start by understanding what is actually happening, not what everyone assumes is happening. The two are frequently different.
02
Diagnosis
We map the situation clearly: what is known, what is constraining, where the real opportunities sit, and where the risks are.
03
Plan Design
Working collaboratively with your team, we build a plan that accounts for reality. Your constraints, your resources, your actual ambitions.
04
Lead Implementation
We support execution alongside the client team, managing workstreams and adapting as conditions evolve through the engagement.
How We Engage
No two engagements are the same. Ours aren't either.
Every client arrives with a different situation, a different set of constraints, and a different definition of success. We do not apply a standard methodology and call it bespoke. Every engagement is designed from scratch around what you actually need.
Project-Based
A defined scope with a clear beginning, a clear deliverable, and a clear end. Suited for organizations facing a specific challenge or opportunity that requires focused, time-bound work. We scope each engagement carefully and staff it to match what the work actually requires.
Fractional
Embedded, ongoing support across one or more functions, without the overhead of a full-time hire. We embed within the client organization on a sustained basis, contributing to ongoing workstreams and producing work product alongside the internal team.
The right advice changes what is possible.
But only if it is actually implemented. Let's talk about both.
Chesterton Hills is a business and strategy advisory firm that works alongside clients through the full scope of an engagement, from initial diagnosis through implementation.
Our Story
Built differently, on purpose
Chesterton Hills was founded by practitioners who observed a consistent gap between advisory work and the implementation of that work inside organizations. That gap is where value is most often lost.
We built this firm to operate across both sides of that gap. We develop the analysis and the plan, and we engage at the level of execution to help clients carry it through.
We work with senior leaders and management teams across a range of industries and organization types, from established companies navigating complex change to growth-stage businesses entering new markets.
"Strategy without execution is pointless. Every plan survives until it makes contact with reality."
Jasper Cannon
Founder & Managing Partner
Industries We Serve
We work across industries. With two exceptions.
Our engagements span a wide range of sectors. The quality of the work does not depend on the industry.
Healthcare & Life Sciences
Technology & SaaS
AI & Emerging Technology
Financial Services
Future of Work & HR Tech
Consumer & Retail
Energy & Infrastructure
Media & Communications
Social Media & Creator Economy
Education & Workforce Development
Travel, Hospitality & Logistics
Real Estate
Agriculture & Food Systems
Who We Work With
Our clients range from early-stage companies to established organizations across the private, public, and nonprofit sectors.
We do not take engagements in vice-related industries, including tobacco, alcohol, gambling, and cannabis. We also do not work with cryptocurrency or digital asset businesses.
Mission & Purpose
Why we come to work every day
Our Mission
To help organizations solve complex problems and build durable capabilities, by working alongside their teams through the full scope of each engagement.
Our Vision
A world where the quality of an organization's thinking and execution determines its success, not its size, its zip code, or its existing relationships.
Our Promise
Candid counsel, a plan built for your actual situation, and a team that stays to lead the work.
What We Stand For
How we work.
Five principles. One standard. Everything we do at Chesterton Hills is grounded in how we believe serious advisory work should be practiced.
CRAFT
C
Curiosity
We begin with questions, not answers. Understanding what is actually happening is the first and most important step toward giving useful advice.
R
Rigor
Our work is grounded in disciplined thinking and careful analysis. Ideas are tested before they are trusted. Conclusions are earned, not assumed.
A
Accountability
Advice has consequences. We take responsibility for the quality of our thinking and the real-world impact of our recommendations.
F
Focus
The most valuable insights are often the simplest ones. We concentrate on the few decisions that genuinely matter and resist the urge to make everything complicated.
T
Trust
Our work depends on confidence earned over time through discretion, candor, and consistent judgment. We protect it accordingly.
Ready to work with a firm that stays?
The value of advice is entirely determined by what happens after it is given. Let's talk about what that looks like for your situation.
AI is only useful if it actually changes how the organization operates.
Most organizations are somewhere between ignoring AI entirely and adopting it indiscriminately. Neither produces results. We work with clients to identify precisely where AI creates genuine operational or commercial leverage, then build what is needed to deliver it, and stay involved through deployment and adoption to make sure it holds.
We treat AI as a capability question before it is a technology question. What does the organization need to be able to do that it cannot do now? We answer that first, then determine whether and how AI is the right answer. If it is, we build it.
All advisory and development work is led by experienced practitioners who understand both the technology and the business problem it is intended to address.
Capabilities
01AI opportunity assessment and use-case prioritization
02Custom AI model development and deployment
03Large language model integration and fine-tuning
04Workflow automation and process AI integration
05AI governance framework and policy development
06Change management and organizational enablement
07Vendor and technology selection advisory
08Ongoing model performance monitoring and optimization
09AI strategy and roadmap development
10Data infrastructure assessment and preparation
11Integration architecture design
12Build-buy-partner analysis
Every AI engagement begins with an honest assessment of whether it will actually move the needle for your organization.
Entering a new market is a sequencing problem as much as a strategy problem.
A market entry that looks sound on paper frequently fails in execution because the sequencing is wrong: the wrong partners engaged too early, the regulatory environment underestimated, the operational infrastructure built too late. We manage the full arc of a market entry, from the initial opportunity assessment through the establishment of a functioning commercial presence.
Our work spans geographic markets across Latin America, Europe, Asia, and North America, as well as new market segments within existing geographies.
Market entry failures are almost always predictable in retrospect. They happen because the business moved faster than its understanding of the market.
Capabilities
01Market attractiveness assessment and sizing
02Competitive landscape and white-space analysis
03Entry mode strategy
04Regulatory and compliance environment navigation
05Local partner identification, assessment, and negotiation
06Commercial model design for new market context
07Operational setup and infrastructure development
08Go-to-market planning and execution management
09Distribution strategy and channel design
10Pricing and margin architecture
11First-year performance management
12Course correction and adaptation planning
We have managed market entries across 30+ countries.
The idea is rarely the problem. What breaks down is the translation from concept to commercial reality: pricing that does not reflect how customers actually buy, go-to-market plans that were not stress-tested against real conditions, operational infrastructure that could not handle real volume.
We work across the full scope of a launch, covering the strategic, commercial, and operational dimensions simultaneously. We stay engaged through the first phase of growth, when the decisions made in the first 90 days tend to determine whether the launch scales or stalls.
Most launch plans are written for a world in which everything goes as expected. We plan for the world in which it does not.
Capabilities
01Product-market fit assessment and validation
02Pricing strategy and commercial model development
03Go-to-market planning and execution management
04Customer acquisition strategy and channel design
05Launch readiness assessment and gap analysis
06Sales process and enablement development
07Operational infrastructure planning and build-out
08Launch performance management and reporting
09Post-launch optimization
10Scaling strategy and capacity planning
11Competitive response planning
12Customer feedback integration and iteration
The first 90 days matter most. We are there for all of them.
The value of a transaction is determined after it closes, not before.
Deals are made or destroyed in integration. The post-merger work, where cultures collide, systems need to be reconciled, reporting structures have to be redesigned, and the original deal thesis has to actually be realized in operations, is where most transactions quietly lose the value that was projected for them.
We support the full transaction lifecycle with particular depth in the integration phase. We work with both acquirers and targets, and we engage at whatever stage in the process we can add the most value.
Most integration failures are not caused by bad analysis. They are caused by underestimating the people dimension and moving too slowly once the deal closes.
Capabilities
01Target identification and long-list development
02Strategic fit assessment and prioritization
03Buy-side due diligence support and management
04Sell-side preparation and data room management
05Deal structuring and negotiation advisory
06Synergy identification and financial quantification
07Integration strategy and workstream planning
08Day 1 readiness planning and execution
09Cultural assessment and integration planning
10Operational integration management
11Post-merger performance tracking and realization
12Carve-out and separation advisory
The 100 days after close determine whether a deal creates or destroys value.
Growth is a design problem. Most organizations treat it as a hope.
Sustainable growth rarely comes from doing the same thing harder. It comes from identifying the right external relationships, the right channels, and the right commercial structures, and then building them deliberately. We work with organizations to design and execute the external-facing components of their growth strategy.
Partnerships are often the most powerful and most mismanaged tool in a growth strategy. The opportunity gets identified, the announcement gets made, and then the actual work of making the partnership produce results gets underestimated. We work on the full lifecycle.
Growth strategy at the level we practice it is not a spreadsheet exercise. It is a set of choices about where to concentrate the organization's limited capacity for external relationship-building.
Capabilities
01Growth strategy development and prioritization
02Partnership opportunity identification and sizing
03Strategic rationale development and validation
04Partner assessment and selection
05Commercial structure and deal design
06Channel and distribution strategy
07Term sheet development and negotiation advisory
08Alliance governance and operating model design
09Joint business planning and commercial alignment
10New revenue stream identification and development
11Customer and market segment expansion planning
12Partnership performance review and optimization
We have negotiated over $1.5B in partnership value.
What a business says, how it looks, and how it is perceived are all the same problem.
Most marketing problems are actually positioning problems. The messaging does not work because the underlying position is not clear, differentiated, or credible. We start with positioning and work outward, building marketing programs that are commercially grounded and measurably connected to business outcomes.
Public relations and communications are not separate from marketing strategy. We manage both functions under one integrated approach.
Credibility is built slowly and lost quickly. The organizations that handle difficult moments well are almost always the ones that built their communications infrastructure before they needed it.
Capabilities
01Brand strategy and positioning
02Messaging architecture and narrative development
03Visual identity and brand system design
04Marketing strategy and annual planning
05Integrated campaign development and management
06Content strategy and editorial planning
07Demand generation and lead acquisition
08Digital marketing strategy and execution
09PR strategy and integrated communications planning
10Executive communications strategy
11Thought leadership development and placement
12Crisis communications preparedness and response
The brand story and the public story should be the same story.
An organization's capacity to execute is ultimately a people problem.
Most growth and operational challenges have a people dimension that gets underdiagnosed. The strategy is sound, the market opportunity is real, and the execution still falls short because the organization does not have the right structure, the right talent in the right roles, or the management systems required to translate ambition into performance.
We work with organizations on the full range of human capital and talent challenges, from org design and workforce planning through executive hiring strategy and compensation architecture.
We also work on culture, not as a branding exercise, but as an operational question. Culture that is not deliberately designed defaults to whatever emerges, which is rarely what leadership intended.
Capabilities
01Organizational design and structure
02Talent strategy and workforce planning
03Executive search advisory and hiring strategy
04Compensation benchmarking and total rewards design
05Performance management system design
06Leadership development and succession planning
07Team effectiveness and capability assessment
08Culture definition and organizational values work
09HR function build-out and operating model
10Org design for post-acquisition or rapid-growth environments
Getting the human capital architecture right early determines how well the business scales.
Distressed situations and underperforming operations are both execution problems.
When a business is under financial or operational stress, the premium shifts entirely to speed and precision. The diagnosis has to be right and it has to happen quickly. We work alongside management teams, boards, and investors to develop and execute recovery plans grounded in what the business can realistically achieve.
We also work with organizations that are not in crisis but are underperforming operationally. Processes that made sense at one stage of growth become bottlenecks at the next.
Whether the situation is distressed or simply underperforming, the underlying discipline is the same: an accurate diagnosis, a realistic plan, and the discipline to implement it under pressure.
Capabilities
01Distressed situation assessment and diagnosis
02Cash flow stabilization and liquidity planning
03Cost reduction strategy and implementation
04Operational restructuring planning and execution
05Creditor and stakeholder communication advisory
06Debt restructuring advisory and negotiation support
07Business model viability assessment
08Management team assessment and realignment
09Turnaround plan development and board presentation
10Operating model design and restructuring
11Cost structure analysis and optimization
12Recovery monitoring and course correction
Distressed situations require a different kind of clarity. We have been there before.
Raising capital is a preparation problem before it is a relationship problem.
Most founders and executives underestimate how much of a fundraise is determined before the first investor meeting. The narrative, the financial model, the answers to questions that will inevitably be asked: all of it shapes how investors form their view of the business, and most of it is set before the conversation begins.
We work on the full scope of fundraising preparation including the investment thesis, the narrative architecture, the supporting materials, and the KPI framework investors will use to evaluate the business.
Fundraising strategy and capital allocation strategy are inseparable. How the capital will be deployed matters as much to sophisticated investors as how much they are being asked for.
Chesterton Hills provides advisory and preparation services only. We do not broker securities, solicit investors on behalf of clients, manage or hold capital, or perform any function requiring registration under applicable securities laws.
Capabilities
01Fundraising strategy and narrative design
02Investor materials and KPI architecture
03Financial storytelling for boards and sponsors
04Capital allocation strategy
05Investment thesis development and articulation
06Financial model review and investor-ready presentation
07Valuation framing and comparable analysis
08Investor targeting strategy and outreach planning
09Due diligence preparation and data room organization
10Term sheet review and negotiation advisory
11Board and investor communication frameworks
12Follow-on raise preparation and positioning
The first investor meeting is won or lost well before it happens.
Chesterton Hills is a business and strategy advisory firm based in Dallas. We hire across levels when the fit and the timing are right.
Why Chesterton Hills
What it is like to work here
Chesterton Hills is a growing advisory firm. We work across a wide range of industries and disciplines, and the people we hire reflect that range. What they share is a high standard for the quality of their work and an interest in being close to consequential decisions.
We are direct about what we are. Our team is lean, the work is substantive, and we hold a high bar regardless of the role.
Direct Access
Our structure is intentionally flat. The people doing the work are close to the people leading it, regardless of role or level.
Substantive Work
Every role at Chesterton Hills exists because the work requires it. We do not create positions to fill organizational charts.
Professional Network
The nature of our work puts you in contact with founders, executives, and investors across the industries we serve.
Professional Development
We invest in the people who join us. That looks different at different levels, but the commitment is consistent.
Principled Environment
We do not take clients in industries we find objectionable. The work reflects that.
Cross-Industry Exposure
Our client base spans healthcare, technology, financial services, and beyond. The range here is wider than most firms offer.
Open Roles
Current openings
Social Media & Marketing Communications Intern
InternshipHybridDallas, TX
Do not see the right role?
We consider candidates at all levels and hire when the fit is right, not only when a role is formally posted.
Chesterton Hills Consulting is an equal opportunity employer. We do not discriminate against candidates or employees on the basis of race, gender, sexual orientation, religion, disability status, age, or any other characteristic protected by law.
Employment Notice
Chesterton Hills Consulting does not sponsor employment visas. Applicants must be legally authorized to work in the United States and willing to complete background checks as part of the hiring process.
We do not work with external recruiting agencies and do not pay referral fees for unsolicited candidate submissions.
Contact
Every engagement starts with understanding the situation. Let's start there.
Tell us what you are working on. We will read it carefully and respond with a candid perspective.
Who Should Reach Out
Not every problem needs an advisory firm. But some do.
You are facing a challenge where the obvious approaches have already been tried, and you need a partner willing to think carefully about what is actually going on.
You are preparing to do something that genuinely matters, whether that is entering a new market, launching something significant, or negotiating an agreement that needs to go right.
You want someone who will engage seriously with your situation and give you a perspective grounded in actual analysis rather than whatever answer seems most agreeable.
Get in Touch
Start with an email.
Tell us briefly what you are working on. We will read it carefully and respond with an honest view on whether and how we might be useful.
We handle all inquiries with discretion. We aim to respond thoughtfully to every message we receive.
What to Expect
What happens after you reach out
01
Understanding the situation
Before discussing solutions, we begin by understanding the situation carefully. Like our namesake story implies, we want to understand your problem before we proceed.
02
Exploring whether we may be helpful
Once we understand the situation, we can determine whether our perspective would be genuinely useful. The goal is simply to identify the most sensible next step.
03
A thoughtful path forward
If it makes sense to continue, we will outline a tailored advisory approach based on the situation you described. Serious advisory work rarely begins with a template.
Partnerships
We work with a select group of firms across complementary disciplines.
If you believe there may be a natural fit, we would be glad to hear from you.
Who We Partner With
We work with a small number of partner firms.
Chesterton Hills maintains a small number of working relationships with firms in complementary disciplines. Each of those relationships is based on our assessment of the firm's approach, quality, and fit with the kind of work we do.
If there is a good fit, we explore the possibility of a formal partnership arrangement, which may include referral agreements and co-engagement opportunities.
What We Look For
—
Evidence of substantive, completed work for clients in a defined area of practice.
—
A clear and defensible area of specialization. We are not looking for generalists.
—
A strong, well-regarded reputation within their field and among their clients.
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Alignment on how client relationships should be handled, with discretion, integrity, and a bias toward doing the right thing.
—
Leadership that operates at a senior level and is directly involved in the work, not just the sales process.
Referral & Revenue Sharing
Partner arrangements.
Where applicable, we have formal written arrangements with partner firms governing referrals and co-engagements. Partner firms operate independently. Chesterton Hills does not supervise, control, or assume responsibility for the work of any partner firm.
Referral Arrangements
Where a partner firm refers a prospective client, any referral arrangement between the firms is documented in a separate written agreement. Referral arrangements do not affect the terms of any engagement between Chesterton Hills and a client.
Co-Engagement
In some cases, Chesterton Hills and a partner firm may each contribute to a client engagement in their respective areas of practice. The scope of each firm's work is defined separately. Each firm is responsible for its own work product and client relationship.
Get in Touch
Interested in exploring a partnership?
Use the form below to tell us about your firm, or reach out directly. We review every inquiry and respond to the ones that look like a genuine fit.
Partnership Inquiry Form
Form coming soon. In the meantime, reach out directly below.
Contact Us
Send us a brief note about your firm, what you specialize in, and what kind of partnership you have in mind. We will read it and respond honestly.
Be sure to label your message to include your firm name and the word partnerships, so it gets routed to the right member of our team.