Director, New Business Sales

Portless; Canada; Remote; CAD 130,000 - 190,000; Full time

Benefits offered by this job

Equity

Full benefits

Remote-first with occasional team ons

Job summary

Portless is seeking a Director of New Business Sales to lead seven AEs selling to SMB and Mid-Market, with global exposure across Asia, Europe, Australia, and APAC. This leadership role emphasizes talent, culture, and coaching, with impact on deals and pipeline, and requires coordination with cross-functional partners.

You will not carry a personal quota but will be judged on team results and talent development, while guiding strategic deal cycles across regions and markets.

Qualifications

• 3+ years of sales leadership experience managing quota-carrying Account Executives.
• Track record as a quota-bearing closer in the mid-market and/or enterprise space.
• Demonstrated ability to recruit great sales talent and retain it.
• Ability to build a team culture that consistently hits commitments.
• Proven coaching ability with tangible rep improvements.
• Track record of winning deals yourself and helping your team win deals.
• Comfort working across time zones including Asia, Europe, Australia, APAC.
• Experience with CRM and sales tools (HubSpot, LinkedIn Sales Navigator, Gong).

Responsibilities

• Recruit and retain outstanding sales talent; own hiring for the new business team as it scales.
• Build a high-performance, low-ego culture with clear commitments and standards.
• Coach at a world-class level through reviews and 1:1s with focused feedback.
• Join deals that matter, shape strategy, engage senior stakeholders, and close with reps.
• Own the number; forecast accurately and diagnose pipeline issues early.
• Run deal cycles across regions with Asia, Europe, Australia, and APAC teams.
• Develop the playbook for winning new business and refine discovery and positioning.
• Partner with BDRs, Marketing, Onboarding, Client Success, and RevOps; maintain CRM discipline.

Skills

Sales leadership

Quota-bearing closer

Talent recruitment

Coaching

Cross-functional collaboration

Dealmaking

Time zone flexibility

Tools

HubSpot

LinkedIn Sales Navigator

Gong

Job description

About Portless

Portless is a tech-enabled supply chain business that helps DTC brands ship directly from Asia to customers worldwide in 5-9 days. We're transforming how ecommerce brands think about fulfillment by eliminating the traditional 60-90 day ocean freight model and replacing it with faster, more flexible, cash-flow friendly logistics.

We're venture backed and growing fast. Our customers include brands shipping everything from apparel to consumer electronics, and we operate in 55+ countries. We're on a mission to make global fulfillment as seamless as domestic shipping.

The Role

We're looking for a Director of New Business Sales to lead the team of AEs responsible for winning new logos at Portless.

You'll inherit a team of seven new business Account Executives selling into the SMB and Mid-Market segments, with ACVs most commonly associated with Enterprise deal values in other industries. These are real deals with real complexity: multiple stakeholders, operational diligence, and buyers who need to move physical product in order to go live with our solution. Your team owns those deals end-to-end, from qualified opportunity through implementation.

This is a leadership role, not a player-coach role. You won't carry a personal quota. You will be measured on whether your team hits its number, and on whether the people on it get better while they do it. That means recruiting and retaining talent others want to hire, building a high-performance and low-ego culture, coaching at a world-class level, and knowing when to put your own hands on a deal.

It's also a global role. Our fulfillment operations run out of Asia, and our customers are expanding into Europe, Australia, and the wider APAC region. You'll work directly with our teams on the ground in those markets and help your AEs run deal cycles across them. The time zones required to execute at a global scale demand flexibility beyond a traditional 9 to 5 and we're looking for someone who treats that as part of the opportunity rather than an inconvenience.

What You’ll Do

• Recruit and retain outstanding sales talent. You'll own hiring for the new business team as we scale beyond seven AEs, build a bench before you need it, and keep your best people here and growing.

• Build a high-performance, low-ego culture where the team makes commitments, meets them, and holds each other to a standard which demands we all do the best work of our careers. You'll set the bar for what "on track" looks like and make missing it uncomfortable without making it personal.

• Coach at a world-class level through call reviews, deal reviews, and 1:1s. You'll use our "One Thing" coaching philosophy to give each AE focused, specific feedback that measurably improves their craft.

• Get into the deals that matter. You'll bring real deal sense to your team's highest-potential opportunities, joining calls, shaping strategy, engaging senior stakeholders, and helping close business without taking the deal away from the rep.

• Own the number. You'll forecast accurately, track leading indicators, and diagnose pipeline problems early enough to do something about them.

• Run deal cycles across regions. You'll partner directly with our team in Asia and support your AEs on opportunities in Europe, Australia, and APAC.

• Develop the playbook for how new business is won at Portless, refining discovery, business case development, and competitive positioning as we scale.

• Partner cross-functionally with BDRs on target account strategy and handoff quality, with Marketing on messaging, with Onboarding and Client Success on customer transitions, and with RevOps on the systems that make the team faster.

• Maintain CRM discipline across the team, with accurate forecasting, clean deal stages, and activity logging in HubSpot.

What We’re Looking For

Must-haves:

• 3+ years of sales leadership experience managing quota-carrying Account Executives.

• Your own track record as a quota-bearing closer in the mid-market and/or enterprise space.

• Demonstrated ability to recruit great sales talent and retain it.

• Demonstrated ability to build a team culture that consistently hits its commitments.

• Demonstrated coaching ability, with specific examples of reps who measurably improved under you.

• A track record of winning deals yourself, and of helping your team win deals you were involved in.

• Comfort working across time zones, including direct collaboration with our team in Asia and deal cycles in Europe, Australia, and APAC.

• Experience with CRM and sales tools (HubSpot, LinkedIn Sales Navigator, Gong, etc.).

Nice-to-haves:

• Experience selling to ecommerce, DTC, or retail brands.

• Familiarity with logistics, supply chain, 3PL, or fulfillment industry.

• Experience with usage-based pricing models.

• Experience scaling a sales team through a period of rapid headcount growth.

• Previous experience at a high-growth startup where you helped build the sales motion.

The intangibles we care about:

• Coachable: You actively seek feedback and apply it fast.

• Capable: Leadership is a craft to be mastered, you care about doing so.

• Curious: When in doubt, figure it out. You are always looking to better understand your prospects, sales as a craft, and the ecommerce industry.

• Resilient: You navigate complex deals and setbacks without losing momentum.

• Driven: You're motivated by achievement and like to compete.

• Low-Ego: If you aren't a team player you will fail here.

Why Portless

Ownership from day one: You'll have a team, a number, and autonomy to run your business.

Coaching culture: Our sales team operates on a "One Thing" coaching philosophy: focused, actionable feedback every week to help you improve.

Product that sells: DTC brands are under pressure to improve cash flow and expand globally. Our value prop is concrete and differentiated.

Growth trajectory: We're scaling fast. High performers will have opportunities to move into senior leadership or new market expansion.

Compensation & Benefits:

• Competitive compensation

• Equity

• Full benefits

• Remote-first with occasional team onsites

Our Hiring Process

1. Recruiter screen (30 min)

1. Hiring manager interview with the VP of Sales (45 min)

1. Case study take-home, reviewed with the broader Sales leadership team (45 min)

1. Cross-functional interview with another member of the Portless leadership team (30 min)

1. Offer