Head of Sales

Ply; Raleigh; Hybrid; CAD 192,000 - 235,000; Full time

Job summary

A dynamic software company is seeking a Sales Leader to drive their go-to-market strategy. The candidate will develop pipeline and sales processes while leading a small team. Responsibilities include building a robust revenue machine and collaborating across functions to enhance customer engagement. Ideal applicants have 7–12 years in B2B SaaS sales and experience scaling revenue from $1M to $10M. A competitive salary and equity options are offered.

Benefits

Generous Equity

Medical

401k

PTO

WFH stipend

Qualifications

• 7–12 years in B2B SaaS sales, with leadership experience.
• Experience in a fast-paced early-stage environment.
• Proven track record of scaling revenue from $1M to $10M.

Responsibilities

• Sourcing and building pipeline for key accounts.
• Taking discovery calls and running demos.
• Hiring and developing Account Executives.

Skills

B2B SaaS sales experience

Team leadership

Deal closing skills

Pipeline management

Job description

Reports to: CEO

Location: Raleigh-Durham, NC or Charleston, SC (Hybrid)

Stage: Seed → Series A transition

About Ply

Ply builds software that helps home service contractors run better businesses — starting with inventory management. We serve trades like HVAC, plumbing, and electrical, helping contractors get control of their materials, reduce waste, and increase profitability.

We’re a team of builders and problem-solvers who value autonomy, collaboration, and thoughtful execution. We care deeply about our customers and the details that make their lives easier. Ply is headquartered in New York City raised $18m+ from leading investors Primary Venture Partners, SignalFire, and Stage 2 Capital.

Ply is well capitalized, ready to professionalize our sales motion, and poised to expand our market footprint.

We’re looking for a critical sales hire to help us scale Ply’s GTM motion, team, and success.

This is a player/coach role. Our hope is to find an ambitious and talented sales professional that can join us, master our existing sales motion while identifying gaps and opportunities, and then elevate our entire GTM motion across all functions. Our intention is that this person has every opportunity to become VP Sales in 12‑18 months.

We believe this is the perfect time to join us and get the best of both worlds. On one hand, we have built a trusted brand, delivered a product our customers love, forged critical partnerships, scaled our customer base, and expanded into new markets.

On the other hand, it’s still early enough to come in and be the architect of a revamped sales motion. We want to implement a repeatable, high‑velocity sales motion, a team that’s built to grow, and a culture that thrives on performance, accountability, and coaching.

If you’re excited by the idea of taking a small but hungry team and turning it into a predictable revenue machine, you’ll fit right in.

What You’ll Do

Player and IC Responsibilities

We envision this role starting as 75% player and 25% coach. Early on we believe it’s best to master the sale yourself to prove your capabilities and develop a vision for how to elevate the entire GTM motion. In your first 12 months, the IC responsibilities will include:

• Sourcing and building your own pipeline for key accounts while the team scales
• Taking discovery calls, running demos, and helping close strategic or high visibility deals
• Co selling with early AEs to help them improve judgment and deal execution
• Jumping into stalled or complex opportunities to help push them forward
• Acting as a direct extension of the founder in important customer conversations
• Set the pace for the team by personally sourcing and closing key accounts

This hands on work helps set the tone for how we sell and supports stronger rep development.

Build and Lead the Team

The 25% coaching scope of your role will include the following, ramping up over time as you get settled into the IC portion of your role.

• Hire, onboard, and develop our next wave of Account Executives as our BDR-to-AE promotion track takes off.
• Shape and scale a sales culture that values consistency, process, and coaching as much as results.
• Lead a growing hybrid team with BDRs in the US and Argentina, plus a small but expanding AE team.
• Partner with our Business Development Manager to refine the training and promotion program for BDRs who are fast‑tracked to AE roles.
• Hold the team to high standards for pipeline creation, deal quality, and execution
• Ensure revenue targets for the quarter are met through tight deal management and coaching

Build the Revenue Machine

We would greatly value your early input and longer term vision for how to build a robust and predictable revenue machine. Some of the areas of exploration and responsibility here will include:

• Design and refine a repeatable sales process from lead to close that fits our outbound‑heavy motion.
• Define key metrics and dashboards across pipeline, conversion rates, and velocity; making it easy to see what’s working and what’s not.
• Introduce (or clean up) tools and processes like CRM hygiene, call review cadences, and pipeline management frameworks.
• Own the sales number and the path from $2M → $10M ARR.
• Set quotas, territories, and forecasting models as the BDR and AE team scales.
• Work closely with marketing on pipeline creation, lead quality, and conversion feedback loops.

Be a True Cross-Functional Partner

• Collaborate with the CEO, Product, and Marketing to sharpen our ICP, pricing, and messaging.
• Work cross functionally to identify new potential verticals to experiment with.
• Be the voice of the customer internally while sharing insights that help shape our GTM strategy.
• Partner with partnerships and marketing to turn feedback into targeted campaigns and better inbound flow.

What You Bring

• 7–12 years in B2B SaaS sales, including at least a few years leading a small, scrappy team in an inside or SMB to Midmarket motion.
• You’ve helped steer a move upmarket by designing a clear playbook for mid market and larger accounts
• You’ve helped take a company from around $1M to $10M in ARR, ideally in a sales‑assisted or product‑led motion.
• You’ve successfully hired, coached, and promoted BDRs into quota‑carrying AEs.
• You’re comfortable in the early‑stage environment where things move fast, playbooks evolve, and you like being part of building them.
• Experience in home services tech, field service management, or similar vertical SaaS is a plus but not required.

The Kinds of People Who Thrive Here

You might come from one of two paths:

• Builder/Operator: You’ve already been a Head or Director of Sales who scaled a company from $1M–$10M ARR and want to do it again — faster and smarter.
• Player-Coach: You’re currently leading a small AE team at a fast‑growing startup and ready to take on your first full sales org — you love leading but still enjoy closing deals yourself.

Compensation

• Base: $140K–$170K + Generous Equity
• OTE: $250K–$300K
• Medical, 401k, PTO, WFH stipend.

How to Apply:

Please send your resume and a brief introduction to [e-mail]. We look forward to hearing from you.

Ply is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, physical or mental disability, age, veteran status or any other basis protected by law.