Milestone Systems Jobs in Florida (NOW HIRING)

Are You Ready to Change the Industry Together? 

Milestone is a tech-enabled, asset-light logistics provider transforming the civil construction supply chain. We’re on a mission to accelerate how infrastructure gets built through smarter movement of materials, technology-driven transparency, and customer-centric efficiency.  As Milestone continues to scale, the Sales Manager plays a critical leadership role enabling our sales organization behind the scenes. This leader is not a quota-carrying seller, they are the performance engine supporting the systems, people, coaching, and processes that make sales successful. Reporting to the VP of Growth Operations, the Sales Manager leads and develops Business Development Representatives, Outside Sales Reps, and collaborates closely with the Sales Operations and Marketing teams, ensuring they have the tools, training, technology adoption, and support required to execute consistently and predictably. This leader embeds Followed By All (FBA) across all sales processes, builds high-performing teams, eliminates barriers, and ensures the sales organization deeply understands and leverages Milestone’s technology, NewMile, to create value for customers and drive growth. 

• Mission: We are a family of brands committed to raising the standard of service in the aggregate distribution industry.  
• Vision: Accelerating the world's infrastructure. 

Our Values   

• 1% Better, Every Day: Continuous growth is a part of who we are as professionals and people. We are committed to being better today than yesterday, so we are ready for who our organization needs us to be tomorrow. 
• Promise & Deliver: Pick up the phone, respond, then get it done. We are reliable in every sense of the word and deliver quality work and customer service no matter our role. We own our areas and are accountable to ourselves and each other to build trust. 
• Find a Way or Make a Way: There is no problem we can't solve. We work together and do hard things to simplify the lives of clients, haulers and each other. We find the best way and are open-minded to innovation, technology and new ways of working because we are building an organization to change our industry.? 
• Candid, but Kind: We tell each other the truth and challenge when we don’t agree. We build real relationships rooted in kindness and thoughtfulness. Our people will always be our #1 unique and we will never lose sight of that. 
• Rev it Up: Positive energy fuels us to get us to our vision. Each of us contribute to our culture by bringing consistent energy and passion that ripples through our teams like a fire. We celebrate and praise each other's contributions and strive to create a place we all want to be. 

Who You Are:  

You are a growth-minded, system-oriented people leader who thrives behind the scenes driving performance. You believe that great sales results come from clear processes, strong coaching, accurate data, and consistent use of technology. You are energized by helping teams adopt new tools, learn how to use them effectively, and confidently communicate their value to customers. You have a natural ability to break down complex workflows, teach people how to execute them, and ensure FBA adoption across the team. You think long-term, build scalable systems, and thrive in a role where developing people, improving processes, and strengthening technology adoption fuels success. 

Why This Role Matters:  

Milestone’s sales organization succeeds when teams are: 

• Well trained 
• Well equipped 
• Well supported 
• Technologically enabled 
• Process-driven 
• Aligned and accountable 

The Sales Manager ensures this happens every day. This role is the backbone of sales execution, leading coaching rhythms, refining processes, improving data integrity, strengthening adoption of both internal and external technologies (NewMile, CRM, etc.), building onboarding programs, aligning systems, and removing obstacles that hinder performance. As Milestone’s technology evolves, the Sales Manager ensures sales teams understand how to use it, speak to it, sell it, and drive customer adoption. 

Who Your Internal Customers Are and How This Role Delivers Value to Them: 

• VP, Growth Operations: You translate high-level sales strategy into day-to-day execution, ensuring the sales organization has the systems, coaching, and process discipline needed to deliver predictable results. 
• Market Leaders & Territory Growth Teams: You provide clarity, alignment, and accountability to ensure Business Development Representatives and Outside Sales Reps execute consistently, support regional priorities, and strengthen customer relationships. 
• Business Development Representatives & Outside Sales Reps: You equip them with the tools, training, coaching, and systems they need to sell effectively, grow gross profit, expand accounts, deliver excellent customer experiences, and communicate the value of NewMile. 
• FP&A/Sales Operations: You partner closely to ensure sales reporting, forecasting, systems, and analytics are accurate, timely, and actionable, enabling strong decision-making and accountability. 
• NewMile Team: You support technology deployment and adoption by ensuring sales team members are trained, equipped, and confident in using NewMile, speaking to its value, and driving customer adoption. 
• Operations & Dispatch Teams: You remove barriers between sales and operations, improve handoffs, and ensure the sales team’s commitments can be executed consistently and successfully. 
• Customers & Haulers: You help elevate the customer and hauler experience by ensuring smooth onboarding, clear communication, process consistency, and a sales team that represents Milestone’s values with professionalism and accuracy. 

What You’ll Obsess Over to Be Successful 

• Being hands-on in HubSpot — personally designing, building, and automating the pipelines, workflows, and processes the sales team runs on, and codifying them into Followed By All (FBA) standards that stay consistent and aligned as the team scales across Texas, Florida, and South Carolina  
• Driving adoption of the CRM and new technology — HubSpot, NewMile, and AI tools — until daily usage is consistent, observable, and coachable, changing behavior rather than just enforcing compliance  
• Equipping reps to confidently speak to and sell NewMile's value to customers and prospects, not just use it internally 
• Removing friction and helping reps focus on the highest-impact activities — cutting low-value work, sharpening weekly priorities, and lifting productivity without adding headcount  
• Energizing and engaging the team — building productive habits, sustaining morale, and re-engaging reps who've lost momentum  
• Coaching, developing, and building talent — diagnosing skill gaps, building development plans, and growing BDRs, Outside Sales Reps, Inside Sales, and Sales Ops into top performers  
• Onboarding and enablement — building the training, playbooks, and ramp programs that get new reps productive fast and keep the whole team equipped on tools and process  
• Elevating deal quality, not just close rate — coaching reps on consultative, value-based selling, rescuing at-risk deals, and pulling in cross-functional support to unblock opportunities  
• Direct performance management — addressing underperformance early and honestly, holding clear standards, and using metrics and data to change behavior and sharpen coaching  
• Pipeline execution, forecast accuracy, and data integrity — prospecting-to-close discipline, clean pipeline, honest forecasting, and the governance and leading indicators that keep CRM data reliable and performance predictable  
• Territory prioritization and gross-profit discipline — aligning coverage to where the growth is, focusing reps on the highest-margin accounts, and coaching toward profitable deals over volume  
• Smooth handoffs across sales, operations, dispatch, and onboarding — defining SLAs and fixing friction so what sales commits to gets executed 

Impact/What You’ll Own & Drive: 

Lead, Manage, and Hold the Team Accountable (LMA) 

• Lead Business Development, Outside Sales, and Sales Operations team members 
• Own the coaching cadence — pipeline reviews, 1:1s, performance reviews, and individual development plans 
• Set clear standards and hold the team accountable to activity goals, process adherence, and results, including direct performance conversations when they're needed 
• Uphold Milestone's values, culture, and expectations of excellence 

Build and Own Sales Systems, Process & CRM 

• Design, build, and maintain the team's pipelines, workflows, and automations in HubSpot 
• Codify sales processes into Followed By All (FBA) standards and audit adherence so execution is consistent and observable 
• Own CRM data integrity, forecasting rhythms, dashboards, and the reporting the sales org runs on 

Drive Technology Adoption & Team Enablement 

• Lead adoption of HubSpot, NewMile, and AI tools — driving daily usage and behavior change, not just initial training 
• Build onboarding, playbooks, and ramp programs that get new reps productive quickly and keep the team equipped 
• Ensure reps can confidently speak to and sell NewMile's value to customers and prospects  

Strengthen Sales Execution & Gross Profit Growth 

• Drive consistency in prospecting, pipeline management, quoting, and account expansion 
• Partner with Growth Operations and Market Leaders to align on pricing, margin, and territory priorities 
• Coach teams toward profitable, high-quality deals — disciplined follow-through and closing, not just volume 

• 5+ years in sales leadership, sales enablement, or revenue operations  
• Experience leading and managing teams of BDRs, Outside Sales Reps, and Sales Operations roles  
• Hands-on CRM expertise (HubSpot strongly preferred)  
• Strong process discipline and a track record of designing standardized sales processes and ensuring adherence at scale (FBA-style execution)  
• Proven ability to drive technology and process adoption and behavior change  
• Experience owning pipeline management, forecast accuracy, and CRM data integrity  
• Ability to communicate complex tools and features simply, and coach reps to sell their value  
• Strong coaching, performance-management, and people-development skills, including direct handling of underperformance  
• Ability to work cross-functionally and solve operational challenges between sales and operations/dispatch  
• Experience with dispatch/logistics tech a plus  
• Thrives in a fast-paced, evolving, high-growth environment 
• Ability to travel