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Talk through your challenges and see if Second Mile is the right partner to help.
Talk through a projectThe work is not finished when the system goes live.
Second Mile is a HubSpot and web partner built for connectivity and IT service providers, with a long track record in higher education, membership organizations, and mid-market B2B. We build the system around how your business runs, then stay to keep it growing as the business does.
Why we started this company.
We kept seeing the same two problems, and nobody was solving either one well.
The first was inside our clients' companies. A CRM that does not talk to billing. Marketing tools that do not talk to sales. A website that does not reflect the organization behind it, and manual work filling every gap in between. The cost is not just inefficiency. It is a sales rep who got into the job because they are great with people, now spending half the day on data entry. It is a marketing team that cannot see what is working because nothing is connected. We understood these industries well enough to know what needed connecting, and we cared enough about the people inside them to do it properly.
The second was inside agencies. The default model, more people, more hours, more output, was burning people out quietly and calling it culture. We believed an agency could do excellent work efficiently and protect the time and energy of the people doing it. Ten years in, that is still how Second Mile runs.
Our team
The people you will work with.
A small team, and everyone on it does the work. When you talk to Second Mile, you are talking to the people who will build and support your system.
Jess Vossler
Chief Executive Officer - Co-founder
Hannah Collins
Co-founder
Sam Crockett
Chief Technical Officer - Partner
Mitch Transue
Senior Account Strategist
Natalie Eadie
Senior Account Strategist
Ryan McGarry
Senior Account Strategist
Jacob Kedra
Growth Strategist
Parker Nokes
Data Architect
Melissa Kalish
Strategic Operations Lead
Work with us.
A four-day week, clients who stay for years, and work that has to hold up after launch. If that sounds like the place you have been looking for, we would like to meet you.
See open rolesThe standards behind the work.
Four values, written down because we hold each other to them.
Live Generously
We have an abundance mindset and strive to exceed expectations.
- We choose to trust there is enough to go around. We look for ways to help our clients, teammates, and partners become better versions of themselves.
Stay Studious
We are lifelong learners driven by the desire to improve.
- We keep expanding our knowledge and skills, challenge the status quo, and stay curious about better ways to solve the work in front of us.
Champion Relationships
Trust is built through truth and care.
- We share what is working and what is not, including bad news, assume good intent, and follow through so that trust builds.
Contribute Solutions
Ownership is how we move forward.
- We raise problems early, own our mistakes out loud, and make decisions with intention rather than waiting for permission.
How we work.
Every engagement, whatever its size, runs through the same three stages. Discovery is part of the engagement.
Map
Understand the work
Your goals, the people involved, and the systems they use. We settle which system owns each fact, who owns each part of the work, and what the first phase should be.Build
Make it work in practice
Strategy, design, and implementation in phases your team can use as they land. We test the work against your real workflows and records, and we explain the reasoning behind every decision as we go.Adopt
Put it to work
Each role is trained on its own part of the system, and the documentation lives inside the platform. By handover, your team runs the day-to-day with confidence. Many clients keep us on for ongoing support and improvement as the business changes.
A four-day company. By design.
Second Mile works a four-day week, and has for years. It works because the same things we build for clients hold inside the company: clear ownership, systems that do the repetitive work, and direct communication. Clients notice it as a team that is present, prepared, and not running on fumes.
Read the four-day week storyCommon questions
Are you a HubSpot partner?
Yes. Second Mile is a Platinum HubSpot Partner and has been an agency for a decade. We build on HubSpot for CRM, marketing, sales, service, and CMS, and we connect it to the billing, membership, ERP, and operations systems our clients already run.
Where is Second Mile based?
Our team is based across North America, Europe, and South Africa. In North America, that includes Nashville, Portland, and Charleston. Most engagements run remotely, with on-site time where a project calls for it.
What does the four-day week mean for us as a client?
A team that is rested and prepared, and a company whose own systems have to work. Client communication, deadlines, and support coverage are planned around the schedule from the start of an engagement, and clients are told how it works before it affects anything.
What does Second Mile not do?
Standalone IT support, quick fixes, social media management, and content-only retainers. We build and connect systems: HubSpot, websites, and the integrations between them and the platforms your business runs on. If the work does not touch one of those, we are not the right partner, and we will say so on the first call.
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