Careers

Who we are looking for

The work at Chesterton Hills happens inside businesses, close to their numbers, their plans, and their teams, and we staff it deliberately. If a career here is of interest to you, we would love to hear from you.

How We Hire

We Hire Intentionally

The nature of our work requires it. This work happens inside businesses, close to their numbers and their plans, and we only hire people we would trust with that access.

Read by humans, not AI

Every application is read by the hiring team. We do not use AI software or tools to filter out applicants. Every application is read by a real person at the firm.

Background checks

Due to the nature of our work, we are often inside a client's numbers, plans, and confidential material. Every applicant must be capable of passing a background check, and any offer is made on that basis.

Referrals are welcome

We are always open to strong candidates who want to join the team, and we accept referrals from anyone, including agencies and placement services. We do not pay any fees for candidates brought to the firm this way.

Work authorization

We recognize that talent is global, and our internships are open across the US and the EU. Chesterton Hills does not provide visa sponsorship of any kind, and our consulting roles are open only to candidates who already hold permanent work authorization in the US.

Application received. It goes straight to the hiring team, and a real person reads every one. If there is a fit, you will hear from us.
Open Roles

Come Join Our Team

Chesterton Hills is a fully remote firm. We hire people we trust to do their best work without an office to sit in.

Solutions Consultant (1099)

You run the firm's sales process from end to end: finding prospective clients, opening the conversation, understanding what a business needs, presenting the services that fit, and carrying the opportunity through to a signed engagement.

  • Prospecting & outreach
  • Discovery & qualification
  • Proposals through close

Chesterton Hills is expanding its sales function. The Solutions Consultant runs the firm's sales process end to end, from first contact through a signed engagement. You will identify prospective clients, work the leads and relationships already in the firm's pipeline, open conversations, understand what a business is trying to accomplish, present the services that fit, manage follow-up, and carry qualified opportunities through to a decision.

The work runs through email, LinkedIn, phone, referrals, and professional networks, and it is built on considered outreach and credible conversations. Firm leadership approves final proposals, pricing, scope, and contract terms, and will join the conversation wherever it helps. Keeping momentum, answering questions, and asking for the business are yours.

The hours are flexible. The role can sit alongside another position or be treated as full-time work, as long as you stay responsive and manage the pipeline well.

What you will do

  • Manage the sales process from prospecting through client commitment
  • Research new prospects while working existing leads, referrals, and warm contacts in the firm's pipeline
  • Run outreach through email, LinkedIn, phone, networking, and referrals
  • Lead discovery conversations, qualify opportunities, and present the services that fit the need
  • Manage follow-up, work through questions and objections, and ask directly for the business
  • Work with firm leadership to finalize proposals, pricing, scope, contracts, and negotiation
  • Keep accurate pipeline records and meet agreed expectations for meetings, proposals, and closed business

What we look for

  • Strong written and verbal communication, and comfort speaking with founders, executives, and owners
  • The ability to run a sales process independently and move opportunities toward a decision
  • A consultative mindset and the judgment to match a need to the right service
  • Comfort with warm and cold outreach, discovery, follow-up, and closing
  • Organization, research, and time management across a live pipeline
  • Self-direction, resilience, and reliable follow-through
  • Comfort using or learning LinkedIn Sales Navigator, CRM systems, and outreach tools
  • Experience in sales, consulting, professional services, recruiting, partnerships, or another complex B2B environment helps, but is not required

Compensation

  • 100% commission, uncapped, based on the business you close. No base salary. 1099 contract position
  • Commission is a percentage of contract value, with a transparent structure and clear payment terms
  • Progressive commission bands available based on performance

Location

  • US applicants only, with permanent work authorization

Social Media Marketing Intern

You help shape how the firm shows up in public: writing and scheduling posts, running the content calendar, turning conversations and appearances into readable content, and tracking what earns attention.

  • Writing & publishing
  • Content calendar
  • Performance tracking

We are looking for a Social Media and Marketing Communications Intern to support communications across the firm's digital platforms and, on a limited basis, selected client engagements. Strategy and final approval of anything published externally sit with the firm's leadership and marketing advisors. Your part is developing and organizing the content and the outreach behind it.

You will draft content, prepare materials, and help carry out communications plans, with regular feedback and direction as you go. It suits someone who likes writing and storytelling, wants exposure to professional services marketing, and is interested in where strategy and communications meet.

What you will do

  • Write and schedule posts across LinkedIn, and selectively on Instagram, Facebook, and X
  • Turn consulting ideas, conversations, and rough notes into clear public-facing content
  • Maintain a forward-looking content calendar tied to firm and client initiatives
  • Draft outreach messages and correspondence consistent with the firm's tone
  • Research the communities, publications, and conversations where the firm should be visible
  • Monitor comments, messages, and engagement, and surface what needs a response
  • Propose posts based on business trends, market news, and client-relevant topics
  • Track performance and summarize what is working, what is not, and why
  • Repurpose longer ideas into concise posts and short-form takeaways
  • Help prepare and promote content around firm and client announcements
  • Keep drafts, ideas, and published work in a simple internal archive

How you will work

  • Produce work you would be comfortable seeing attributed to a respected business publication
  • Deliver on agreed timelines and keep projects moving
  • Propose topics and next steps without waiting for assignments
  • Distill complex ideas into publishable material
  • Use judgment about what is appropriate for a professional audience
  • Ask questions when you need to, and make reasonable calls without step-by-step instruction
  • Help shape the process and standards for a role that has no existing playbook

What you will bring

  • Pursuing or recently completed a bachelor's degree in Marketing, Communications, Advertising, Public Relations, or a related field. We will also consider candidates without a degree in progress who can show a strong body of content work
  • Excellent writing and editing
  • Organized, proactive, and detail-oriented
  • Curious, and interested in learning quickly
  • Interest in brand strategy, executive communications, or B2B marketing
  • Helpful: experience creating and editing short-form video
  • Helpful: demonstrated social media or digital content experience

What you will gain

  • Portfolio-worthy work reflecting real brand positioning for a professional firm
  • Exposure to how firms build credibility in competitive markets
  • A professional reference for future applications or graduate school
  • A working understanding of how content contributes to reputation and client acquisition
  • Our support in working with your university toward course credit

Location

  • US and EU applicants only

How to apply

  • Submit your resume, and a portfolio link if you have one
  • Portfolio work from internships, clubs, coursework, or personal projects all count
  • A document linking to relevant work is perfectly acceptable

Investor Relations Intern

You support investor relationship development and capital readiness for client companies: researching aligned investors and their mandates, preparing briefing materials, and helping coordinate introductions across the firm's network.

  • Investor & mandate research
  • Briefing materials
  • Introduction coordination

You will work with firm leadership on investor relationship development and fundraising strategy for client companies. The role sits where consulting, venture, and partnerships meet. You will help identify aligned investors, prepare for conversations, coordinate introductions, and maintain relationships across the firm's network.

The work is relationship driven, and success is measured by the quality of the relationships built. A smaller group of investors who trust the firm, take the meeting, and engage seriously is worth far more than a long list of names who never reply.

The boundary of the role matters. You are not raising capital and you are not negotiating deals. You are helping make sure the right introductions happen and that both sides arrive prepared. What follows is up to them. The firm does not raise capital on behalf of clients, act as an intermediary, or take part in negotiations; our role is advisory and connective.

Many of the most relevant investors are not immediately visible and do not advertise what they are doing. Finding them takes persistence, curiosity, and a willingness to follow threads other people ignore. Initiative shows quickly in this role.

You will be speaking with investors, founders, and partners on behalf of the firm, which asks for judgment, responsiveness, and a steady level of professionalism. Credibility is built through consistent follow-through, and it compounds.

What you will do

  • Maintain the firm's investor relationship records, including outreach tracking, meeting notes, and history
  • Research venture funds, private equity groups, angels, and family offices for alignment with client companies
  • Prepare briefing documents and summaries ahead of investor conversations
  • Help prepare the materials clients use to communicate with investors
  • Draft professional correspondence, including outreach and follow-ups
  • Coordinate introductions between investors and client companies
  • Support fundraising strategy by tracking engagement and preparing insight
  • Attend selected networking events and investor meetings representing the firm
  • Monitor your local investment ecosystem and flag relevant opportunities

What we look for

  • Enrolled in an undergraduate or graduate program, preferably Business, Finance, Economics, Entrepreneurship, or a related field
  • Exceptional written and verbal communication, and clear professional correspondence
  • Professional presence and comfort dealing with executives, founders, and investors
  • Highly organized and detail oriented
  • Strong research ability and comfort synthesizing information
  • Interest in startups, venture capital, private markets, or business strategy
  • Familiarity with the startup and investment ecosystem
  • Familiarity with Google Workspace or Microsoft Office
  • Helpful: experience with CRM platforms such as HubSpot, Notion, or Airtable
  • A significant bonus: involvement in investing, venture, finance, or entrepreneurship clubs and competitions

What you will gain

  • Direct exposure to how fundraising strategy and investor relationships work in practice
  • A clearer understanding of how investors evaluate companies, opportunities, and markets
  • Practical experience with founders, executives, and investors
  • Insight into how a firm supports growth, strategy, and capital readiness
  • An expanded network across your local startup and investment ecosystem
  • Familiarity with how opportunities are sourced, evaluated, and pursued in private markets

Location

  • US and EU applicants only

How to apply

  • Submit a resume
  • Optional: writing samples, research, or project work showing communication or analytical ability

Equal opportunity

We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other characteristic protected by law. If you need an accommodation at any point in the process, tell us in your application and we will make it work.