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Seeking advice for transitioning into a career in high tech sales with no sales background


Jack Shepard Southern Pines, NC

I am an active duty Army Soldier wanting to transition to a career in high tech sales by July when my terminal leave starts. I’ve served nine years in both conventional and special operations as an Infantryman in the 82ND Airborne Division and as a Civil Affairs Team Sergeant in the 95TH Civil Affairs Brigade. I have extensive experience and multiple deployments leading anywhere from four to eight-man elements in the Airborne Infantry and four-person teams in Civil Affairs. My latest role as a Team Sergeant in Civil Affairs is what piqued my interest in sales and customer success. While deployed, my job required developing or maintaining relationships with key stakeholders in foreign militaries and governments. The quality of those relationships dictated the freedom of movement my team and I had in whichever country we were operating in. I very much enjoyed pursuing and interacting with potential key stakeholders and organizations in foreign countries. I was able to develop leads that were valuable to my team’s mission success and also created mutually beneficial relationships that are still in effect today. I genuinely believe I was able to develop and maintain relationships with partner nation forces because of the soft skills I acquired in the Infantry. Leadership, teamwork, self-discipline, adaptability, and excellent communication skills allowed me to quickly and easily gain buy-in when developing relationships.

Although I have no “sales” experience or a formal business education on my resume, I feel I can translate my job experience to a sales role. To expand my knowledge of the business and sales sector, I am currently enrolled in online courses through Harvard Business School (Business Analytics, Economics for Managers, and Financial Accounting). I will attain the HBS CORe Credential of Readiness in April, and I will be able to better understand and speak to C-suite executives, team members, and customers. Furthermore, I’m beginning to learn Salesforce, and I have confidence I will be a certified administrator before Spring.

I’m currently working with recruiters to find and apply to a 3-4-month internship/fellowship starting in April. Under the Army Career Skills Program, servicemembers are given the opportunity to do an unpaid internship/fellowship at a company with a potential job offer, within 180 days of ETS. I want to possibly find an internship at companies with strong sales training such as Cisco, HP, Dell, Microsoft, Adobe, Zoom, Salesforce, HubSpot, SAP, etc. However, I don’t think it is possible for the recruiters I’m working with to generate such an opportunity. I think I will have a better chance of landing an internship or sales job in the high-tech industry with the right guidance and mentorship.

Please let me know if you’re available to talk or would like me to send you my resume/Linkedin. I want to figure out if I’m heading on the right path or what further steps I should take to better my chances of employment. Thanks!

27 January 2019 17 replies Mentoring



Steve Wittenberg Danville, CA


My company, IBM, has a focus on New Collar jobs (not blue collar or white collar…new collar; “It’s not about the degrees, it’s about skills”). Check it out here:

We also have an initiative to hire veterans. Check that out here:

I think the skills you describe are highly transferable to a high tech sales job. Feel free to shoot me a note at if you’d like to discuss.

Good luck.


9 February 2019 Helpful answer


Donald Gourley Reading, MA


Check this site out.

Tech sales training for veterans, by successful veteran sales experts. I went Harvard with the founders, and they are the real deal.

God Speed,

29 January 2019 Helpful answer


William Munroe Dunstable, MA

Hi Jack
After a 10 yrs in the US Navy, I transitioned to the hi-tech world in product management and marketing. I spend a lot of time with sales teams and have managed inside sales teams. What you are asking to do is going to be difficult - and you are going to find that even with all your excellent experience most companies are going to be skeptical. You are also going to find the job a real challenge at first until you figure out the nuances of selling to businesses.

As a start, search companies looking for "inside sales" (ISR) roles. Most of these are starting positions and you will be competing with kids coming out of college. Your experience becomes and advantages for you. The career path is from ISR to field sales rep to major account manager. ISR base will be $60K and you can earn up to $100K on commissions. Field sales bases starting is around $90K but you can earn up to $200K in commissions. The big money is being a major account or area manager - then your base is $140K and you can easily earn $300K in commissions.

A quick Indeed search will find many. There are two types - working at an appointment setting company -
These companies teach you everything you need to know, but the pay is lower. After two years of success here it is easy to jump to a company ISR role.

Here is an ISR role at Hubspot

They are often looking for those first two years of experience - but you never know and I will search these out and send in your resume.

I am happy to review your resume and cover letter templates and have a conversation about strategies that will help get you where you want to go.

You can reach me at

Best Regards

28 January 2019 Helpful answer


Sotir Koev Washington, DC

Feel free to check these guys out


Randy Chunne Joshua Tree, CA

Unless you have connections you might have to start at ground zero. You can move up quick because of your leadership skills and your experience but do not expect to get a supervisory role right out of the gate. Find a Company you like and contact the someone who can tell you what they are looking for. Use LinkedIn to meet people who work there and talk to them. Network. My biggest kickback was that I might have to start lower than I wanted to be, but with determination and leadership your potential is limitless.


Kimberly Smith Chicago, IL

Hi there - check out -- we hire many sales people regularly across the nation and look for the right personality and skill set, not just experience. Many of the roles apply nicely to the military when it comes to technology with a big focus lately in cyber security so it might be a good fit for you!


Sean OShea Palos Heights, IL

Hello Jack and many thanks for your great service to our country! After reading your message above, I have no doubt that you can be successful in sales. You showed the key ability to map what your experience and strengths are to the activities and strengths needed in a sales professional! Many experienced salespeople struggle to do what you've successfully done. I've been in hi-tech sales for over 20 years and would be happy to share some ideas with you. You can reach me at


Ray McGarrigal Danbury, CT

Thank you for all you have done for America. Your thought process is spot on in understanding
the links in relationship selling. I would suggest you expand your thinking beyond high tech hardware selling. You may be able to increase your chances in other areas e.g. software.
Salesforce is a perfect example. Every sales person needs to understand their product as well as their competition. You will soon be certified in Salesforce. Study their competition. Then send a letter of introduction to their CEO Marc Benioff. You will need to do some homework before sending the letter so you can get his attention. I would be glad to help you with that task. Let me know if you would like to connect. Again thank you for your 9 yrs. of service.


Aubrey McDonald II Fayetteville, NC

Good morning Jack, Thank You for your Selfless Service.

I'm interested in Speaking with You.

Give me a Call at 910 578 9860



Jo Prabhu Long Beach, CA

You are right in that Recruiters may not be able to help find the job/s you seek as we are retained by companies to find those who are experienced in any field.


Jerome Wong Scarsdale, NY


Thank you for your service. As you are looking to break into tech sales with an unconventional background and experience, it is important that you can explain why you want to get into tech sales and why you would be good at it. You are asking a hiring manager to take a risk by hiring you so it is important to bond with the manger at an emotional level; which, not coincidentally, is what successful salespeople do with their clients. This requires introspection on your part to be able to convey your sincerity so that the hiring manager will take the risk on you. Happy to discuss further if you are interested.




Jim Rohrbach Evanston, IL

Hi Jack! I coach sales professionals to grow their clientele. Email me your resume and I'm happy to help you pro bono.


Bob Molluro Wilmington, DE

Jack I teach people how to become a "Killer Interviewer". If you want to do a one hour free session just let me know. Warmly, Bob Molluro
My email is if you want to make sure we connect immediately.


Bob Molluro Wilmington, DE

Jack there are some very good answers so read carefully. Looks like you have a great background and the "goohonies" to pull off a career in high tech sales. Since I worked for two high tech companies IBM and Amdahl , here is what I would recommend. The key will be who you are working with or mentored by especially in the first year. Here are some of the "jewels" I picked up from my mentor at IBM.
1) When you are selling to companies try to understand their strategies and craft your solutions to fit them. Many people are just selling product. When you learn how to become a consultative sales person they will buy all the stuff in your sales manual.
2) When you are assigned sales objectives (we use to call them quotas). You need to develop a written plan. The plan should reflect how you are going to attain 300% of your assigned objective. You probably will never attain it and fall short. However, you will be the only one who knows. In my seven years as a sales person for IBM I averaged 220% of assigned quota and became one of the top 12 producers out of 8,000 at that time.
3) The person you work for will probably have 12-15 people he is managing. He is spending about 90% of his time worrying about himself. The other 10% is spent on the 12 -15 people. If you are the new kid on the block how much time do you think he is spending on you? Look around as there are always people willing to help. Make friends with the other top producers and get them to guide you.

I could go on. The key is you are a self starter. Always take responsibility for the results you produce and never point fingers. You will make mistakes which are expected. Learn from them, correct them and move on. Just listen to any successful pro athlete say "I'm just trying to get better each day." Success comes from persistence. Able to take a punch and get up to keep fighting. I am willing to bet you already knew that. Good luck. Warmly, Bob Molluro


Emanuel Carpenter Atlanta, GA

Jack - I have over 14 years of sales experience and have written books on sales process. Your military career is impressive, and you have done some great things to get ahead of the curve when it comes securing a sales job (like getting certified in Salesforce and taking classes through Harvard).

Unfortunately, without having a degree and actual sales experience, you will be limited in regards to what sales positions you secure. So here is what I suggest:

1. If you want to sell for tech companies, start by taking ANY job that gives you actual sales experience. It doesn't matter if you're selling cars, insurance, or Amway. If you're not selling enterprise-level software, some tech companies might hire entry-level sales reps but it's a longshot. Recruiters and hiring managers care more about actual selling experience than education. After 6 months of non-tech sales experience, start applying for sales positions at high-tech companies.

2. If there is a specific company you want to work for, see if they have sales development rep or business development rep (SDR or BDR) positions available. Many of the positions are entry-level, and you will work with a lot of people straight out of college. In this position, you don't close deals. Instead, you research prospects, cold call, send emails, and book meetings or demos for the closers on your team. After a year or so, this position can often lead to a closing role within that same company. During the interview process, ask if the company has an SDR to AE training program.

3. Work on getting the degree. Many employers require the degree simply to weed out the rift raft. They also use it to ensure you know how to learn.

4. On your resume, highlight these military skills you've already obtained: diligence, early-riser, coachable, leadership, optimism, competitiveness, team player. Also, sales leaders want their reps to be money hungry.

5. Employers won't care so much about the details of what you did in the military if it doesn't translate to the specifics of what you will be doing as a sales rep. So, include the high-level things of what you learned in the military and leave out the details.

6. Read books that teach you how to close deals. Two that I highly recommend are "The Challenger Sale" by Matthew Dixon and Brent Adamson and "The Lost Art of Closing" by Anthony Iannarino.

7. Find out who the VP of Sales is at the company you want to work for and ask to connect with this person on LinkedIn. When they connect, ask them for advice on the best way to get a sales job there. Who you know is still just as important as what you know. And the best positions are often found through personal referrals and not job boards or classified ads.

Best of luck.


Jack Shepard Southern Pines, NC


I'm currently interviewing with them as we speak. I appreciate your reply!




Jack Shepard Southern Pines, NC


I appreciate your response! This is definitely the type of feedback that I need. I'm sending you an email with resume/CL, as well as some other avenues I'm considering approaching.



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