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.
Every application is read by the hiring team. We do not use AI software or tools to filter out applicants.
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.
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 contract Commission only Remote Flexible hoursChesterton 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.
- 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
- 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
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.
- US applicants only, with permanent work authorization
Investor Relations Intern
Internship Remote US and EU applicants Investor & mandate researchYou 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.
- 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
- 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
- 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
- US and EU applicants only
- Submit a resume
- Optional: writing samples, research, or project work showing communication or analytical ability
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.
The work happens close to their numbers, their plans and their teams.
Remote · read by humans · every application answered
Apply.
Tell us which role you are after in your three sentences. Every application is read by the hiring team, and we do not use AI software or tools to filter out applicants.
Every application is read by a real person at the firm. Any offer is made on the basis that you are capable of passing a background check, and we do not provide visa sponsorship of any kind.
Application received.
It goes straight to the hiring team, and a real person reads every one.
Send it to a person, not a filter.
If a career here is of interest to you, we would love to hear from you. Questions about a role, a referral, or your own timing are welcome by email.
Social Media Marketing Intern
Internship Remote US and EU applicants Writing & publishingWe 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.