Director of Sales

Shipware, LLC - San Diego, CA (30+ days ago)

Director of Sales – Shipware, LLC (San Diego, CA)

An Exciting Goal! Time is valuable. If you are a winner – this is the place for you. If not, mahalo

Shipware’s passion is to utilize experience, IP and technology to help businesses reduce parcel (FedEx/UPS/DHL) and LTL trucking costs while improving transportation spend management. Our tagline is Shipping Expertise – Savings Delivered.

17 years of success and industry leadership, earning 2017 honors in INC 5000 and SDBJ Fastest Growing Private Companies for growth of 525% (2014-2016). Leadership has invested millions in growth of colleagues, technology, new office space, process improvement and marketing. This is a culture of competition, growth and fun.

We are seeking an organized, effective communicator, experienced, highly motivated and competitive Sales Manger to lead and grow our team.

This is a salaried position with uncapped commissions that requires a successful track record of listening, planning, working hard, training/leading, interpreting and executing ownership vision/strategy while engaging new clients and kicking ass. A winner must be able to execute both strategically and tactically.

The Challenges You Will Face

The market is maturing and we face multiple competitors. This can be a long sales cycle with many buyers/stakeholders involved in the decision. Shipware is a high-end consultancy – we must get in front of the decision maker. You need to understand the industry, the buyer, the personal and professional wins, the strengths and opportunities of our sales team – and prioritize your valuable time for best outcomes.

What it Takes for You to WIN

If your character looks like this: extroverted, active listener, ask good questions, lead, network, communicate well, have high attention to detail, love to compete/win and are money motivated – this may be for you.

Company Background:

Shipware provides expertise and technology to help companies reduce parcel/LTL shipping costs 10-30%; without disrupting operations. Our team of industry experts leverages over 200 collective years of carrier pricing experience to help shippers negotiate superior carrier contract terms and pricing. Shipware’s proprietary technology audits weekly invoices to recover refunds on all billing errors, ensuring carrier and contract compliance. Shipware’s cloud-based reporting platform delivers powerful analytics for greater visibility empowering clients to make intelligent cost-saving transportation decisions.

What you get with Shipware, as Director of Sales:

  • Current sales team of 7 professionals
  • Competitive base salary ($100-$150k DOE)
  • Uncapped commissions (commissions match base salary at plan, and total compensation can easily exceed $300k)
  • Participation in profit sharing and potential for discretionary bonuses
  • Health Benefits
  • Expense reimbursement
  • Private company strength and flexibility; we are debt-free and highly profitable
  • You will have a seat at the Executive Table. You will own and drive new revenue
  • Our commitment to your training and career development
  • 17 years of company excellence and a sterling reputation


  • Hit revenue goals and sales success metrics by successfully managing the sales team
  • Manage behaviors and activities of Sales Team
  • Run weekly Sales meetings and training/Development
  • Run quarterly reviews with each sales rep
  • Manage recruiting, objective setting, coaching and performance monitoring of sales reps
  • Manage lead distribution
  • Manage conference attendance, performance, lead gen
  • Generate new business through prospecting, acquiring, and developing strategic partnerships
  • Develop and maintain accounts using a systematic method of sales skills and techniques (Example: Strategic Selling/Sandler Sales Training) helping our partners generate new business opportunities for Shipware
  • Make persuasive group presentations
  • Manage multiple projects and partners
  • Commitment to customer service with a sense of urgency

Qualifications & Experience:

  • Track record of success in securing new revenue, managing sales teams, working directly with company owners
  • Highly motivated with strong competitive drive
  • Strong network of logistics professionals (not required, but bonus)
  • Work independently with a strong work ethic
  • Excellent negotiation skills
  • Work within a team environment
  • Excellent phone communication and presentation skills
  • Computer skills including Microsoft Office products (Word, Excel, PowerPoint and Outlook)
  • Industry experience is a plus

Candidates Must:

  • Be able to “sell the invisible”. Sell personal and professional “wins”. Sell via business case
  • Never be satisfied with the size of their current pipeline
  • Have proven ability to drive the sales process from plan to close
  • Want to earn more each year by closing new business
  • Be committed to a comprehensive prospecting plan
  • Demonstrate the ability to work according to Shipware's core values: integrity, entrepreneurial, forward thinking, outperform, trust and respect, work hard/play hard, and extreme ownership

Minimum Requirements:

  • 5 plus years of successful sales management experience in mentoring less tenured reps into Sales Professionals while consistently exceeding corporate revenue objectives
  • Digital marketing and channel/partnership familiarity a plus
  • Successful, proven sales track record
  • Strong written and verbal communication skills
  • Must possess strong analytical, strategic selling and creative thinking skills
  • Must be able to effectively use a CRM system. We utilize Salesforce.
  • Experience in the transportation/logistics sales arena is preferred

All applicants must use the following link and complete the assessment to be considered:


Job Type: Full-time

Salary: $100,000.00 to $150,000.00 /year


  • Sales Management: 5 years


  • San Diego, CA