Rupa Datta, Owner, Portfolio People and Club Growth Director, Toastmasters International

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I reached out to Rupa in order to get a Toastmaster’s view on sales and sales presenting, but ended up getting much more – Rupa is also an entrepreneur, a very good salesperson, and actively helps others further their own career though her company Portfolio People.

In a serendipitous turn of events, Rupa now works with us here at The Exceptional Sales Career, where her organizational skills and infectious personality will be exceptionally good for us.

You can read Rupa’s full biography here


Jamie: Rupa, what have you found most fulfilling about your career in sales thus far?

Rupa: The people that I’ve met, how I’ve grown as a person, and how my influencing skills have also got better.


Jamie: Is that the same in what you’re doing right now?

Rupa: Yes, and no. I would argue that everybody is in sales to some extent. My actual job title in corporate life is Key Account Manager for a software company. Functionally, that sits under our customer experience department, but account management certainly has elements of sales to it. I wear several different hats, and as an entrepreneur, by definition, that means you have to sell.


Jamie: Could you tell me a little bit about that relationship between entrepreneurialism and sales?

Rupa: I would say that anyone who is either an entrepreneur or has entrepreneurial ability tends to be the face of their company, and certainly in start-up mode, they need to sell their company.


Jamie: You mentioned being a salesperson within a big company and an entrepreneur. How have you ensured that you’re able to have both simultaneously?

Rupa: I have a business called Portfolio People, which essentially helps people understand and establish portfolio careers, which essentially means most do multiple things at once. Therefore, there is a crossover between paid work and other aspects of your life. When I was approached, and discussed going back into corporate life, one condition was that I have other projects, which I believe can add value to your business. Therefore, I didn’t want to compromise on them.


Jamie: Why do you think it’s so important that people have these other elements in their lives?

Rupa: Because we are not our jobs. Long term, you can get so caught up in living paycheck to paycheck. I’ve seen it happen throughout my career. Yeah, someone might be a top performer, but all of a sudden they can get fired in a petrol station somewhere on the motorway. Are any of us in positions where if the worst happened, it would be within our control?

Portfolio careers are a way to play your career game. Do you know, if you got to let go from the position that you’re in, that you’d be okay for at least a year, or where will the next revenue come from?


Jamie: So it’s about having multiple revenue streams?


Rupa: That is one aspect of it, but it’s also networking, and about having something to do. 

If I were to get fired tomorrow, am I comfortable that I’d be okay financially for a little while? Yes. It’s more than that.

Do I have things to do and people in my network that will open some doors for me? That’s why I’m probably more confident and comfortable than someone who only focussed on their professional job.


Jamie: How has having a portfolio career benefited you personally?

Rupa: I think I am a walking-talking portfolio person. Going back to the part about an entrepreneur; being the person that sells their business the best, I understand that more now than ever before. If I could just digress for one second, and explain what a portfolio career is, it’s about having more than one form of paid work or revenue stream, always learning something, and also getting satisfaction in work that you wouldn’t necessarily find financially rewarding.

How has it benefited me personally? I’d say more so than anything else, it’s opened my eyes up to the value of having a network. Going back to my previous statement, yes, there are people within those facets of what I do, that will always be friends, more than anything else.


Jamie: How would you go about selecting activities outside of work to include in your portfolio? 

Rupa: It starts with what your interests are. We’re at that point where people make New Year’s resolutions and set goals. Sometimes it’s about just working out what weaknesses you have and how that could maybe benefit you in the future, certainly in the short- to medium-term. Will Toastmasters always be a part of my portfolio? Yes, because I continue to grow as a result of it. That said, if I could find additional time for other things, what activity would I take up this year? Probably golf. It might help with my business networking.


Jamie: What coaching would you give people to help their employers understand having a portfolio career? 

Rupa: Like with anything, the employer might be a company, but within the company are the people. A good starting point is how forward-thinking that business is. In my recent experience, I’ve only seen people who think it’s an issue if the other part of the portfolio can be seen as a competing business. But beyond that, it’s not usually a problem.

Sometimes it is harder if you’re going for a new opportunity, and there needs to be some sort of trust built. Equally, in my case, I was very open in my interview as to what I do outside of work, and I was able to sell that to my employer.


Jamie: Would it not be an advantage in many cases? 

Rupa: Absolutely. I think more, and more of that is becoming the case. People often feel too scared at the interview if they’re just thinking, “I need a job first to have these conversations.”


Jamie: Do you think a portfolio career is right for every salesperson?

Rupa: I think a part of it depends on the person and the industry they’re in. By definition, all of us at some point in our lives will have a portfolio. If I was to take a typical career journey, should somebody have a portfolio in an early sales career? I’d say yes. The limitation could come in where maturity could play, or lack of maturity can play a part that would cause detriment. In terms of having a portfolio career, it’s good to have that for variety and diversity before one chooses to specialize, absolutely. Certainly, in the latter part of one’s career, it’s a given that the sales career and family would be your main portfolio elements. 


Jamie: So it might help choose an industry to specialize in? 


If I think back to my generation, when I graduated, it was a given that you start somewhere and you stay in it. There is research out there that now that suggests people in their 20s should experiment a bit more, and then specialize in their 30s. I’d also suggest that everybody, at some point in their career, should have a bit of a dabble. Sales is one of the best training grounds for having a career, full stop.


Jamie: Why do you think that is?

Rupa: Resilience. Everyone needs to have some experience in handling rejection. Sales, historically, has been treated as a negative profession, but it doesn’t need to be. Again, it depends on the industry. If you look at the professional services industry; most salespeople in that industry are at the top of the food chain rather than at the entry-level. It’s actually the young professional graduates that are delivering the work, as opposed to winning the business.


Jamie: What makes salespeople highly valued by their company?

Rupa: Again, it varies from company to company and industry to industry. Three things spring to mind when a high performer is very well regarded and can negotiate their own portfolio career as a result.


I’ve certainly seen it where people have had technical expertise before they go in sales, certainly mid-career professionals in engineering and computing. That’s when they realized that technically they’re very good and functionally they’re very good, but for them to go to director level, they need to then go into sales, and that becomes its own career path.


When I was in business school, a number of my colleagues were very highly regarded project managers and engineers, and the MBA was an entry route to be more customer-facing. I go back to my own experience in the value of having a network or multiple networks and seeing more interlink. When people start to realize the value of that network, that’s when you become more valued.


Jamie: What elements of culture would make a sales organization successful?

Rupa: Arguably, every organization needs to have a sales function, whether or not they call it that. Without sales or new fresh blood, or “land and expand” type attitudes, a business will die. So, culturally, if there isn’t an emphasis on sales, then a business will die, or an organization will die. However, if it’s overvalued and other functions are not rewarded appropriately, that also causes challenges.


Jamie: How do you recommend organizations best compensate their salespeople? 

Rupa: A lot of discussions I’m having at the moment, both internally and externally, are around the total reward package. A typical new business salesperson is very hungry and driven by commissions and bonuses. I think personally and culturally, the way the world is going, balance is equally valued. I can think of a lot of people that are in the sales team in the company that I work with, and financial reward aside, they love the ability to have autonomy and control over their diary. Obviously, it’s results-based, so that speaks for itself. Being able to do the nursery run in the morning makes a world of difference. I’d even say it’s perhaps because there is a male-female divide. A lot of discussions that I’ve been having internally recently have been around, what does fair look like? It’s not necessarily earning in the hundreds of thousands, what does fair look like in terms of reward?


Jamie: On the split between new business and account managership: do you feel like they should be compensated equally?

Rupa: Again, it varies from company to company and culture to culture. Do I think there should be more of an even split than has historically been the case?

Traditionally, in most companies, new businesses is rewarded, and culturally everywhere you get rewarded for signing up for a new phone contract because you’re a new customer rather than an existing customer, and that kind of thing ought to be changing as well.


I think there are different elements to it. There’s the company stance, but there’s also the individual reward and the team reward. They are potentially three layers. If you look at a total reward package, have I made a big deal of influencing and negotiating nonfinancial rewards really well? Yes. Would I want more in the way of equity when it comes to financial reward? Yes.


Jamie: You sound like you’ve had success throughout your career negotiating internally. What advice would you have on that? 

Rupa: I wouldn’t say I’ve had success throughout my career negotiating internally, but I would suggest that it has been something that it’s common to develop over time, partly through age, experience, and wisdom, and partly because I have been in a sales environment throughout my career. I also now understand that there is a bigger picture, more than just going to work, getting a salary, and going home. In terms of giving advice, it starts with the confidence to know what you want. More importantly, understand why you want it, and communicate that accordingly. Don’t ask, and you won’t get.


Jamie: Do you think it’s harder for women to do that in the workplace?

Rupa: Yes. There are cultural barriers. Women don’t tend to ask, or if they do, it’s historically been in the context of having a family and wanting flexible working hours. Is it changing? I’d also suggest yes, but it’s still going to take a little while.


Jamie: How would you test for a good sales culture within an organization?

Rupa: One of the advantages I have in being in Toastmasters, given that we have several corporate clubs is you get the opportunity to visit corporate organizations and get a feel for the culture where most people don’t. Then you’ve got Glassdoor, and you’ve got platforms that you need to rely on. 

I don’t know if you can put it down to the sales culture, but definitely culture, in general, is a massive thing. You should be testing for whether or not it’s appropriate, or if I want to be in that environment.

I go back to my network. I only joined the organization I’m now involved with because I had worked with someone before who was already there, had become a friend, and was able to be very honest for me about the positives and negatives before I made the decision to go through with the purchase.

Jamie: In terms of those people who have decided they definitely want to be in sales, what advice would you give them?

Rupa: If they’ve decided that they want to be in sales because of the earning potential, then fine. I think there’s a particular type of salesperson in that demographic, but in terms of those who are interested in making it a career with a full stop, they’re probably starting in a good place, because at every point in your career you need to sell. My main advice is to remember that the sales cycle is a lot bigger than one aspect of what one does.

For example, I’m just having a conversation with a friend who’s currently job hunting at the moment, you can look at job adverts, and they’ll say, “Business Development Manager.” What does that actually mean? That varies from company to company. In some cases, it’s very much new business, in which case, you should say “New Business Development Manager.” I think over my career, I’ve come to realize and understand that business development covers a lot of different aspects, and that could be from marketing, all the way to account management. We’re always in some sort of business development.


Jamie: If you were starting your sales career again, what would you do differently?

Rupa: I’m proud to be able to say, I don’t think I’d do anything differently. I’m very lucky that even at the time, but certainly in hindsight, I definitely had good mentors very early on. I learned a lot very quickly, and like most people, I fell into sales. I don’t think I’d change anything.


Jamie: Could you tell me about a time when you didn’t make a sale, but you learned something really valuable?

Rupa: One example that springs to mind was quite early on when I started Portfolio People, someone I loosely knew through LinkedIn was introduced to me, had a requirement, we met, and we agreed on a fee. About a week later, they went back on it. Sometimes you get too hungry for the sale and don’t realize that some people aren’t a good fit. I’m glad it happened, and that it happened when it did, as much as I would have loved the revenue. What became very clear in our interactions later was; actually, this would be a bit of a nightmare client.


Jamie: Conversely, in terms of the time when you did make a sale on it, it shows off all of the skills and the knowledge you gained right in career? 

Rupa: I think I find where I do make a sale; certainly, the ones that I remember, it tends to be a pre-existing relationship. I can think of a customer that I have at my day job. They had been a previous customer in a previous life, and now I actually feel like I’m part of the family. I’m going to go see them in a couple of weeks, and one of them has just got engaged, and I’ll take him a bottle of champagne. There needs to be a fit in terms of product or service, but it tends to be my main success is where there’s been a pre-existing relationship.





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