About Karissa Bentley · Founder of InsideOut
I get into the details that keep coming back to you.
I’m Karissa Bentley, founder of InsideOut Strategic Growth Co. I help service-business owners solve problems across operations, systems, and sales—and help put the changes into practice.
Maybe you’re chasing estimates, answering the same questions, or spending your evening catching up on admin. Maybe the next opportunity needs attention, but the work you already have takes all of yours.
I look at what’s happening between the people, tools, and decisions involved. Then we work out what needs to change, who needs to own it, and how to keep it moving.
Based in Richmond, Virginia. Serving Central Virginia and working remotely.
The experience behind the work
Investigation. Implementation. Sales. Operations.
My background spans large organizations and small service businesses. I’ve investigated problems, helped customers navigate unfamiliar tools, improved procedures with frontline teams, and built relationships that expanded existing business.
That experience shapes the questions I ask—and the work I can take on after we’ve identified the problem.
Finding out what’s actually happening.
Fraud investigation and risk analysis taught me to follow the evidence, check assumptions, and notice where information doesn’t line up. I bring that same care to understanding a stalled workflow or a recurring business problem.
Helping people work through change.
I’ve helped establish customer and employee advocacy efforts and gathered frontline feedback on bottlenecks. Working across teams—including legal, risk, and procedure writers—helped me connect policy decisions to the people carrying them out.
Making tools useful in everyday work.
My implementation and onboarding experience includes helping business customers understand products and use their systems. I also build intake flows, automations, trackers, and estimating tools around the work a team needs to do.
Building relationships and moving sales forward.
I’ve worked in cold outreach, referrals, account expansion, bids, proposals, and opportunity research. I understand the follow-through involved in earning business, developing a relationship, and helping a customer use what they bought.
Experience described here includes prior roles and independent project work. Organizations and clients are not named.
A practical change people could keep using.
In one prior role, billing took a concentrated 3–5 hours every Thursday. After reviewing the process, I changed it to 10–15 minutes of daily processing, with about five minutes for the weekly submission.
That routine became the ongoing way the work was done. It’s the kind of improvement I look for: something useful that fits into the working day and can be sustained.
What working with me looks like
We start with the work in front of you.
I’ll ask you to walk me through a real example: the inquiry that wasn’t followed up, the estimate still waiting, or the information someone has entered three times. I want to hear from the people doing the work and understand what they need to get it done.
Then we consider the whole picture. A faster estimate helps when you have capacity to deliver. More leads help when someone can follow up. An automation helps when the information and decisions behind it are reliable.
Depending on the agreed scope, I can build the workflow, connect the tools, organize your pipeline, document responsibilities, or take on ongoing operations and business development tasks. We make ownership, deliverables, and next steps clear.
Listening for the problem behind the words.
An owner might say, “I can’t keep chasing everybody,” or “We have leads, but nothing seems to happen.” Those descriptions give us somewhere to start.
Human Language Mapping (HLM) is a research method I’m actively using and refining. It connects the way people describe their needs with relevant services, resources, and next steps. I use it to inform prospect research and messaging, checking sources, context, and fit before treating a signal as an opportunity.
Your existing tools are part of the conversation.
Examples of tools I’ve worked with include Google Workspace, Microsoft 365, Zapier, Jotform, LEAP, Salesforce, Airtable, and Base44. I also use AI tools for research and workflow support, with source checks and human review.
That list is a starting point. I learn how your team uses its systems and assess what can be simplified, connected, or improved. My website-related work focuses on integrations with intake and business systems.
Tell me what keeps landing back on your plate.
I work with contractors, subcontractors, and professional-service businesses that need help with operations, systems, or sales. You can start with one problem—or a few things you suspect are connected.
Tell me what’s happening and what you need to work better. We’ll discuss fit and a practical starting point.