Founder @MSP Consulting | Enterprise Sales for Startups | $2M => $10M ARR

Most founders aren't bad at sales. They’re just alternating between winging it and following playbooks that were built for companies 10x their size.

I never planned on a career in sales (I studied international relations). But when I fell into sales I realized it was the same skill…understand a situation deeply, then tell a persuasive story around it.

The further I got, the more I kept seeing the same thing. Companies hit the same walls at the same stages and made the same (avoidable) mistakes. And most of the advice for founders was either way too complicated or built for someone else's business.

I didn't want to manage bigger teams at bigger companies. I wanted to help founders solve those problems before they burned 12-18 months figuring it out the hard way.

I work with B2B SaaS founders between $1M–$10M who are building enterprise and midmarket sales orgs. I help them cut through the noise, find the highest-leverage fix, and build something repeatable — without overcomplicating it.

No generic advice or playbooks borrowed from $500M companies. Just proven frameworks built for your stage. 

Book a strategy session below. You’ll leave with clarity on the biggest thing slowing you down right now, and how to fix it.

Monica Stewart

Jeff Hollihan, MBA

Sunshine Behavioral Health

I lead our customer success team, client satisfaction, and alumni functions with a focus on aligning our admissions, marketing, and client success teams to maximize client care. My work includes managing client lifecycles, change initiatives, and strategic projects, with a strong emphasis on data analysis and metrics-driven management to enhance operational efficiency and achieve operational goals.

Manager, Customer Success

4 Squared Business Solutions

I deliver repeatable success to organizations through direct coaching and knowledge across processes, programs, tools, and best-practice leadership strategies. I provide assistance to early-stage and small businesses to get their revenue teams aligned and processes on track or ramped up for growth. 

I offer general project based consulting and interim leadership solutions, but people also hire me for:

- Process Optimization - Metrics, Training, Scale
- Methodology - Processes, CRM, Territories, 
- Team Development - Hiring, Roles & Responsibilities, Compensation Plans
- Enablement Content / Playbooks
- Analysis - Reporting, Dashboards, Team Goals & Quotas

Either on a project basis or as a interim leader I am eager to support your growth initiatives. Please connect with me here on LinkedIn, or email me at 4squaredbusinesssolutions@gmail.com or call me directly at 303-625-3051.

RevOps Consultant/Interim VP of Sales and Customer Success

Rocky Mountain Baseball Club

Rocky Mountain Baseball Club is a non-profit organization that aims to provide athletes and coaches an opportunity to learn and teach the game of baseball in a way that instills a lifelong love for the game. We are dedicated to encouraging our players' positive social, emotional, and physical growth while also building excellent sportsmanship, character, and confidence. Our objective is to develop lifelong memories while assisting in the growth of strong, respectable players who possess the self-assurance necessary to excel at the next level of baseball, but more importantly as future leaders in our community.

Founder

RevOps Co-op

Member

RevGenius

RevGenious is a group of revenue-generating sales and marketing professionals brought together to learn, share, support, and grow with each other.

Bunny Studio

Bunny Studio is a creative fulfillment platform that allows you to get ready-to-use voiceovers, audio ads, written content, translations, video, and dubbing. Bunny Studio's technology is designed to fulfill your creative projects easily and efficiently. We match the best-suited professional from our talent pool to your project and screen the work carefully before delivery. 

I implemented a globally distributed sales team with a focus on driving new customer acquisition of partnerships and clients. In addition, created a sales process, implemented sales methodology practices, and drove process improvements.

Consultant & Vice President of Worldwide Sales

Health eCareers

Prior to my role being eliminated, I managed the Healthcare Division of Health eCareers (an Everyday Health Company) that included Outside Sales, Inside Sales, Account Management, and Account Coordinators. 

I was responsible for setting strategic objectives and creating tactical solutions for sales and customer success teams to drive growth and provide business and customer insights. I refined sales processes, built sales enablement resources, and implemented consistency in communication and employee development activities. I led a 20-person team through a difficult year of changing market conditions while driving new product implementations, sales growth, and improved customer satisfaction results.

Director of Sales and Customer Success

ServiceSource

ServiceSource is an outsourced go-to-market services provider that delivers B2B inside sales, customer success, renewals management, and channel management solutions on behalf of enterprises worldwide.

Led multiple global Customer Success and Inside Sales teams.  Played a strategic role in building creative solutions that are focused on customer satisfaction, revenue retention as well as growth and expansion.  In addition, I proactively managed the customer relationship for the entire lifecycle. This meant identifying, developing, automating, and optimizing processes, tools, and methodologies that led to customer expansion and maximized efficiencies.

Led successful launches of multiple inside sales, business development and customer success teams. These teams included global lead generation/qualification, cross sell/up-sell and end-to-end sales cycle motions.  In addition, led and participated in the creation of strategies to drive product adoption, awareness, and customer satisfaction throughout the duration of the customer life cycle.  I also evaluated customer projects, needs, and business to drive maximum value for customers and defined and owned key performance and engagement metrics for the teams.

Strategic Sales Manager

CLEAR (clearme.com)

Through a secure ID platform, CLEAR is changing how people live and work, creating a more secure, connected world. We transform your eyes and face into a touchless ID, allowing you to quickly and securely confirm your identity - unlocking frictionless experiences across the physical and digital world.

I served as the conduit between sales analytics and field leadership to drive process improvement and supported over 450 employees and more than 50 GM's, managers, and supervisors. Working with cross-functional teams. My focus was on helping to optimize structure, process, tools, and metrics while ensuring alignment to organizational goals.

I collaborated with internal partners: Operations, Marketing, Business Development, Customer Success, and Product teams to guarantee the success of new product launches and drove decisions that successfully grew our business and membership rates.

Director, Sales Excellence

New Horizons Computer Learning Centers / 5 Point Enterprises

Provided corporate and personal training solutions that turn ambitions into marketable skills and business goals into tangible results.  

Managed the overall sales process by setting appropriate metrics and driving accountability, I led technology optimization efforts and embedded solutions within the organization.  I identified and implemented CRM best practices and mapped all related processes to drive the effectiveness and efficiency of the sales force.

Regional Sales Director

I bring together experience in customer success, sales, and operations to help organizations grow smarter and faster. Over the past two decades, I’ve worked across multiple industries and company stages, giving me the ability to spot opportunities from different angles and connect the dots between teams, processes, and strategy.

What I’m most passionate about is helping people and businesses thrive. That means coaching and developing high-performing teams, aligning sales, customer success, and marketing around the customer journey, and building scalable processes that drive growth. Whether it’s working with founders, executives, or front-line leaders, I focus on creating clarity, efficiency, and measurable results.

Some of the areas I bring expertise in include:

   •   Customer Success leadership and journey mapping
   •   Sales and RevOps strategy, including enablement and playbooks
   •   Cross-functional alignment between Sales, CS, and Marketing
   •   Process optimization, metrics, and reporting
   •   Team coaching, development, and change management

Outside of work, I enjoy time with family and friends, coaching youth baseball, golfing, and spending time outdoors.

If you’re looking to connect on growth leadership, customer success, or operational excellence, I’d love to start a conversation.

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The Battle

Monica Stewart

Jeff Hollihan, MBA

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