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Winning by Design sales resource review

Hi, I’m Alex! I’ve been working in sales for innovative startups like SoftBank Robotics and large corporations like NBC Universal for years. Now, I work as an industry mentor at Pathrise. I help people land great sales jobs through workshops and 1-on-1 mentorship. Check out my review of Winning by Design.

What does Winning by Design do?

Winning by Design is an online sales resource that offers training courses and coaching to sales professionals. Their program teaches people the skills they need to land entry level sales jobs or level up their careers. 

They currently have 4 open sales courses on sales fundamentals, prospecting, customer success, and frontline management. All courses last 4 weeks with one live 2-hour session per week. The program meets live over Zoom. Students also get access to recorded videos, hands-on exercises, sales blueprints, and a formal certificate upon graduation.

Sales fundamentals

The sales fundamentals course teaches current account executives the sales best practices that they need to improve their performance and accelerate their careers. Since companies use this program to onboard new sales reps, it can be a good fit for individuals who want to prepare for a new role on their own. The curriculum covers SaaS sales methodologies, effective communication, creating urgency with critical events, storytelling for sales, utilizing strong demos, and the differences between trade and negotiation. Students also get a blueprint they can use to ace their discovery calls as they learn to diagnose with question-based selling.


Sales development representatives (SDRs) in the prospecting course learn communication techniques to craft effective emails and voicemails, as well as best practices to optimize their prospecting time. The curriculum teaches students SaaS methodologies as they craft customer-centric emails and voicemails. Students learn to convert leads with compelling storytelling and how to overcome objections. In addition to learning how to secure AE handoffs, students get blueprints they can use for effective unscheduled calls and qualification calls.

Frontline management

The frontline management course is for new sales managers, newly promoted sales reps in leadership roles, and sales reps who want to become managers. The curriculum teaches students to effectively manage a team by creating a coaching culture, running 1-on-1s, and leading team meetings. In addition, they learn how to use roleplays and call reviews to improve the team’s performance. Students also learn to structure coaching cadence as they master high impact coaching.

Customer success

The customer success course is designed to help current customer success managers (CSMs) and account managers (AMs) optimize account management and grow their accounts. Students learn to orchestrate key moments in the customer success journey like sales hands-off, kick-off calls, and customer conflicts. The technical curriculum covers SaaS sales methodologies, SPICED handoffs, impact orchestration, customer interactions, storytelling, impact reviews, time management, trade, and how to deal with difficult conversations. Students also learn strategies for effective customer communication via meetings, email, phone calls, and video.

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Who is Winning by Design for?

Current salespeople who want to accelerate their careers or prepare for a new role could benefit from Winning by Design’s training. The program is especially helpful for people seeking flexible online training with hands-on exercises, roleplaying, and blueprints they can use on the job.

What does Winning by Design cost? How much work is involved?

The sales, prospecting, and customer success courses cost $1,500 each. Tuition for the frontline management course is $2,500. 

Unlike many other training programs, Winning by Design does not have any formal admissions process. Although their courses are recommended for current salespeople, technically anyone can enroll.

Ratings and reviews

Winning by Design has received mostly positive reviews. They hold a perfect 5/5 star rating on G2, where students described the program as “well designed and engaging!” A new SDR liked that the curriculum was accessible, explaining that they taught the “foundations and best approaches to handle prospecting.” The student also “enjoyed the pre-work (videos, how to guides, quizzes, etc.) to the live session” and was confident that the hands-on practice helped students master the material. However, the grad wished there was an “additional session to practice more in individual groups so we can have more live feedback.” Other students also wished that the course was longer. A few students felt spacing could help, commenting that “more frequent sessions instead of longer sessions with a full week in between” would be beneficial.

The training program holds a 9/10 rating on TrustRadius. One grad praised the curriculum, satisfied that it “takes the best of ‘old’ and ‘new’ sales methodologies” with “great hands-on sessions with lots of interaction.” Overall, students enjoyed the curriculum and experience. But, some would have liked the program to be a bit longer with shorter sessions so they could have time to digest everything they were learning.

Alternatives to Winning by Design 

If you choose not to enroll in a Winning by Design course, there are a number of alternative bootcamps, communities, and resources that can help you start a career in tech sales.

  • The online sales bootcamp Flockjay teaches people the skills they need to launch a career in B2B software sales. They offer an income share agreement (ISA) so students don’t pay until they land a job. Learn more about Flockjay in our review.
  • Another flexible sales course is Prehired, which has remote, self-paced courses to help students launch a career in software sales.
  • Tradecraft is a tech bootcamp and immersion program that offers courses in sales, product design, growth marketing, and more. Their 12-week program is for people looking to land a job at a high-growth startup. 
  • Students on a budget can look into Aspireship. Their free bootcamp helps people become account executives at a SaaS company. Like Winning by Design, the program is remote and includes self-paced learning.
  • People who want real job experience can look into Vendition. Their program teaches sales skills to students looking to find an entry-level account executive position. They offer an “apprenticeship” program that finds students a tech sales job first then trains them for it, offsetting tuition costs.
  • Similarly, both SV Academy and Always Hired are sales bootcamps that pair students with companies so they don’t have to pay tuition. However, students can pay upfront so that they can work anywhere.
  • In the same vein, students at Fuel Sales Academy work while learning and actually get paid during the program.
  • You can also consider The Brooks Group, which teaches online courses and workshops on a variety of sales topics.
  • Similarly, Software Sales Gurus offers online courses for aspiring salespeople.
More alternatives
  • Another sales bootcamp option is Headstart Academy, which is online and self-paced. They also give a job guarantee to students.
  • Women who want to learn sales skills quickly can check out TalentMinded Women in Tech Sales Bootcamp, which lasts 5 days.
  • The online bootcamps GrowthX Academy and Richardson Sales Performance offer courses in sales, business development, growth, management, and more topics.
  • You can also consider TechPoint Sales Bootcamp, which has short internship opportunities throughout the course.
  • Merit America is a nonprofit that teaches tech sales and software engineering to people without college degrees.
  • Another remote and self-paced program, Udemy hosts over 100,000 courses in tech sales, digital marketing, software engineering, and more. Their courses take on a video lecture format and include lifetime access. Classes only cost about $10 each.
  • The online learning platform Udacity offers both free and paid courses on a variety of tech subjects, including business analytics, digital marketing, and growth product management. Students in their “nanodegree” programs work 1-on-1 with both a technical mentor and a career coach as they build portfolio projects. Read more about Udacity in our review.
  • The popular educational platform Coursera offers both free and paid sales courses taught by professors at accredited universities.
  • Similarly, edX is a learning platform that hosts online courses from top universities like Harvard and MIT as well as big tech companies like Microsoft. Learn more about edX in our review.

How does Winning by Design compare to Pathrise?

Winning by Design offers training courses to help salespeople launch and accelerate their careers. While they teach professional skills that students can use in their job search, their program does not actually include career services. Pathrise is a full service organization that helps people with all phases of their job search. Fellows in our program work with experienced mentors to optimize their resumes and LinkedIn profiles, build their portfolios, find recruiters, send cold emails, prepare for technical and behavioral interviews, negotiate salaries, and much more. Our experienced industry mentors have already helped 800+ people land great tech jobs. 

The Pathrise schedule is flexible. Fellows in our program only have 2-4 hours of group sessions per week and can schedule 1-on-1s when needed. The Pathrise income share agreement (ISA) means that fellows don’t pay anything until they land a job they love and start working. We never require upfront payments or deposits. 

Pathrise is a career accelerator that helps students and professionals land their dream job through 1-on-1 mentoring. Fellows in our program have seen their application responses triple, landing jobs in only 3-5 months on average. If you are interested in working with any of our mentors to optimize your job search, join Pathrise. 

Apply today.

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Alex Immel

Alex Immel is one of Pathrise's leading negotiation consultants.

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