32 Financial Services Pros Share Their Biggest Sales Challenges

 In Blog, Wealth Management

Sales is a challenging field, no matter what industry you’re selling in. But financial services sales representatives face a set of unique challenges. Selling intangible products or services is no easy feat, but when you’re selling services that involve the management of clients’ money, such as investment services, money management services, or even accounting services, developing trust with potential clients is imperative. After all, you can’t trust just anyone with your hard-earned money.


Financial services sales representatives must take on a consultative role, providing valuable education and resources that enable prospects to make informed decisions about who they can trust with their savings or income. And when it comes to acquiring new clients who may already have established, trusted relationships with other financial advisors or service providers, it’s even more challenging to gain prospects’ attention and convince them to take the risk of making a major change in how their funds are managed or invested.

Because selling financial services is such a complex role, we decided to gain deeper insights into the key challenges faced by financial services sales pros and how to best overcome these challenges. We asked a panel of financial services representatives and sales professionals to answer this question:

“What are the biggest challenges in selling financial services to clients, and how do you overcome them?” 

Find out what our experts had to say below.

Meet Our Panel of Financial Services Representatives and Sales Pros:


David WaringDavid Waring


David Waring served as a top executive at Forex Capital Markets LLC, which he joined as an initial employee and grew to a publicly traded company with over 700 employees. Since then, David has launched several successful websites. His flagship site, Fit Small Business, offers small businesses the information they need to make the best decisions possible. His most recent project, Fit Biz Loans, helps connect small business owners and entrepreneurs with a variety of lenders to ensure the best and least expensive loans possible.

“The biggest challenge in selling financial services is a common challenge in B2B sales…”

Getting your message to the right person, whether that means getting them on the phone or keyed into your emails or another side of your sales strategy.

I’ve always found content marketing to be a highly effective tool for two reasons: for one, you’re getting yourself in front of interested clients. For another, though, you’re able to screen these potential customers based on what content they’re interested in.

For example, if a visitor to my loans site, Fit Biz Loans, is mostly interested in startup loans, that’s a clear sign they’re not a customer we want to talk to right now – it’s very hard for startups to get financing. That doesn’t mean they’ll never be a good customer, but it is a sign they won’t be eligible for a loan for a while. So we won’t typically call those customers, but we will key them into our email marketing. On the other hand, if someone spends a long time on an SBA loans article that states clearly that two years in business are required, that’s a sign this customer is exactly who we want to talk to.

So content marketing fulfills two purposes. It’s a great way to get in front of potential clients, and you can easily tell their interests and assess what kind of product or service would be right for them, and whether or not your business would be a fit.

Ryan GeorgeRyan George

Ryan George is the Managing Partner of an insurance agency and a Financial Rep for Luttner Financial Group (LFG) located in Pittsburgh, PA. Ryan has been the Managing Partner of his agency for over a year and a half and has been at LFG for the past 5 years. His first year in the business he was ranked in the top five new reps in the country and this year will be making the Million Dollar Round Table (MDRT) top 1% of insurance sales worldwide.

“The single biggest challenge for any financial service rep is…”

Becoming a great teacher. By being a great teacher you are able to educate clients properly and help them make informed financial decisions. The toughest thing that I see is that companies market their products so strongly and they teach their reps to do the same, thus the rep believes (which most of the time isn’t their fault) that what they have is the only product that the client should invest in. We run across so few clients that actually are open to all sorts of diversifying (due to marketing) that it makes it hard for them to understand why they need to do such a thing.

An example would be AIG. They had the, “What’s your number?” ads, basically telling the average household to pick a number out of thin air (or they would help you pick one) and save for that number. The problem with this theory is you can’t plan for disasters along the way (i.e., premature death, disability, new addition to the family, child now being financial responsible for parent, child going to med-school, etc.).

The way we overcome these obstacles at LFG is by taking a holistic approach to selling. We look at all areas of the client’s life and advise them carefully on what decisions should be made, even for products that we don’t sell, making it easier and more comfortable for the client to make a decision. We view ourselves more as the head coach and advise them on how to make plays throughout their earning years and well into retirement.

Brent DickersonBrent D Dickerson, CFP®


Brent Dickerson is owner and financial planner at Trinity Wealth Management in Lubbock, TX. He has been a CFP® professional since 2007 and holds a master’s degree in personal financial planning from Texas Tech University. He is currently pursuing a PhD in the same field at TTU. He is also a chairman of the Financial Planning Association of West Texas and a member of both XY Planning Network and the National Association of Personal Financial Advisors (NAPFA).

“From my perspective there are four challenges that I face continually…”

1. Financial services such as personal financial planning are intangible. It’s not like trying to sell a car. The customer can’t peek under the hood, kick the tires, and take a test drive. We delve into a lot of personal information and sometimes even some personal information that isn’t necessarily about finances. Things that people guard and put defenses around. So, selling financial planning services is more about selling trust, objectivity, and empathy. All things that are very difficult to qualify for consumers.

2. Clients, or prospects, don’t always want to hear what you have to say. This is particularly true when the discussion turns to Estate Planning or Insurance Planning. Having to face the fact that one day you will die and that you need to plan for that is difficult for some people to work through. Defense mechanisms engage and people shut down. It is a difficult task to get people to understand the need for life insurance or setting up trusts to handle their money, property, etc., after they are gone. For some, denial is a very powerful emotion that is hard to get around with financial services.

3. It’s not always about selling products. Product sales by brokers and agents is easy. If you need life insurance, you can simply go to an agent and get some. If you want to buy some shares of Apple, you can simply go to a broker and buy some. People often think that insurance and investment sales is financial services. Many people just don’t understand the concept that there are people (particularly Certified Financial Planners) whose job is to take into account investments, insurance, estate planning, retirement planning, tax planning, and so much more. The hard part here is to get people to understand that many CFPs and financial planners don’t sell products. A lot of us work for the client and not the brokerage firm or insurance provider. We don’t all sell products; some of us sell a service.

4. Lastly, skepticism is prevalent these days. A lot of people are just afraid that financial service professionals are out to take their money. People want to know that their finances are safe, so they look for name brands, large institutions, and the like. As I am a sole proprietor and very small, it is hard to have people understand that they can trust their finances with me better than a one-size-fits-all mega-corporation.

Jason HullJason Hull


Jason Hull, CFP® is the CTO for myFinancialAnswers, a comprehensive online financial planning service for individuals, employers, CPAs, and advisors. He holds a BS from the United States Military Academy at West Point and a MBA from the University of Virginia. He previously co-founded and sold a software consultancy.

“We see two main challenges in selling automated financial services…”

1. Trust. This has multiple components. Do people trust giving their financial information to a web-based service? Do they trust that we have the capabilities to take their data and calculate meaningful results from it? Do they trust that the recommendations that we make are unbiased and in their best interests? Do they trust that we can do as well, or better than, the guy/gal they know who has a franchise investment advisory service in the strip mall in the main street in town?

2. Why not do it myself? Because of the proliferation of information on the Internet, it’s very tempting to believe that if someone Googles enough, they’ll find the right answer. And, in about 80% of the cases, that’s true, assuming that they’re a) willing to put in the time, b) can use critical thinking to sift the bad from the good and then apply it to their specific situation, and c) have the discipline to implement and stick to the plan. After all, financial services usually isn’t rocket science; live by a few basic maxims, and usually success follows.

A lot of people are also very price sensitive. Because of the proliferation of information on the Internet, the median expected price is free. There’s also the perception of free when facing, for example, the aforementioned franchise strip mall investment advisory firms because those costs are not salient and up front in the buyer’s eyes. There is no check written out specifically to the provider, so, perceptually, the service appears to be free, even if it’s far from free. Therefore, providers who do charge up front have to create a value comparison that shows what the buyer is and is
not getting.

Dave BookbinderDave Bookbinder


Dave Bookbinder is a Director of Valuation Services at GBQ Consulting, where he helps his clients with the valuation of businesses, intellectual property, and complex financial instruments. More than a valuation expert, Dave lends his business experiences to help people with a variety of matters. For more about Dave, or to schedule a conversation, visit his LinkedIn profile.

“I find the biggest challenge in selling financial services to clients is…”

My area of financial services pertains to valuation consulting. The business is largely referral-based, where accountants and attorneys (or another trusted advisor) are typically the ones who are closest to the transaction that their clients are in the process of and they are the ones who advise the clients that a valuation is needed. The trusted advisor will usually provide several names in order to give their client the chance to vet and select who they want to work with.

The biggest challenge that I face is the low cost provider – the ones who are willing to perform the services at Wal-Mart pricing. These are either sole practitioners, many of whom are in transition and working from their kitchen tables, or firms that are desperate to keep their employees busy. Most times the client doesn’t get what they really need – a classic case of you get what you pay for. The problem here is that because the other trusted advisor made the referral, the client presumes that all are equal and the only differentiator is price. This is not the case.

James MawsonJames Mawson

James Mawson is a freelance copywriter and web marketing consultant based in Melbourne, Australia. He has worked for various financial services clients, including property development financiers and retirement planners.

“The biggest challenge in selling financial services is…”

Presenting your service offering in a way that addresses the hopes, ambitions, concerns, and anxieties that the customer brings with them. Financial services professionals are generally quite excellent at describing their work in clear, straightforward, and impersonal terms. They are often less proficient at establishing rapport and trust with a customer and communicating what their work can mean for a customer’s day-to-day quality of life or for peace of mind. In addition to presenting the factual case for your services, it is crucial that it addresses this set of more emotional motivations and objections the customer has. This is often the critical point at which the sale is won or lost.

Timothy BakerTimothy Baker


Timothy Baker, CFP® is the Founder and CEO of Wealthshape LLC, a firm built on the belief that investment advice should rely on long term, proven academic evidence and everyone should have access to it. Wealthshape engineers advanced, institutional grade portfolios that are responsibly delivered at a low cost to investors from all walks of life.

“The biggest challenge in selling financial services to clients is…”

Differentiation. The public often lumps all financial advisors together unlike other professions that have a measuring stick to quantify a reputation or skill set. Medical degrees, law degrees, and teaching certificates represent recognizable benchmarks for their professions. Our proud service men and women use a chain of command that instantly indicates their level of responsibility. Financial designations help, but the industry is no where near others in terms of perception. I think much of the public still views their advisor as a broker and vise versa. Changing that narrative will take time and education.

Dinh Xuan TungDinh Xuan Tung


Dinh Xuan Tung is the co-founder of ibox mPOS (an analog to Square that is operating in Southeast Asia). Tung has 10 years of experience in e-banking projects.

“I think the biggest challenge in selling financial products is…”

To be in line with or even exceed customer expectations in simplicity, speed, and availability in remote channels. There are two types of customers: those with traditional behaviors and the ones who have already changed.

Mobile traffic became bigger than desktops this year, according to comScore. Millennials (or Generation Y) are already ruling the world. Almost 50% of the total workforce is expected to be comprised of members of GenY by 2020. These people expect financial products to be simple, available for an immediate buy-in via smartphone or tablet at any moment they want, with a fast reward.

At the same time, when new technologies and consequent behaviors arise, past habits are still sourcing the fat portions of revenues, usually more than 80% of income. And the other challenge is not to forget to feed this healthy cash cow, polishing your value proposition and business processes, and, so to say, keep parasitizing on the regular customers despite the fact that new ones are coming.

Monica Eaton-CardoneMonica Eaton-Cardone


Monica Eaton-Cardone is the co-founder and COO of Chargebacks911, a risk mitigation and chargeback management firm that specializes in fighting friendly fraud.

“One of the biggest challenges we find in selling financial services to clients is…”

Earning the trust of potential customers.

The nature of our business is chargeback mitigation, a subject long considered taboo. We have found that merchants are embarrassed to admit that they have a chargeback problem. Getting them to address the “elephant in the room” is hard enough, but convincing them that they may not be able to combat it alone provides an additional challenge.

We encounter a lot of misconception through misinformation. Merchants operate under the notion that their chargeback situation is normal; just a cost of doing business. We find merchants base normality on their own
historical data and not through comparison to real industry statistics.

Earning the trust of potential customers is one of our biggest challenges. Chargebacks911 guarantees the highest ROI in the industry. It may sound too good to be true, and even though we deliver on our promises, it is hard for merchants to believe. Before they see the results, clients are skeptical that someone outside of their business could win more disputes than their inside team could. In fact, in special cases, we have piloted our services to Blue Chip companies in order to prove that we make good on our promises. The final results are so powerful that the pilots turn into clients. Ultimately, the proof is in the pudding.

Robert PalidoraRobert Palidora


Robert Palidora is a registered representative who offers securities through AXA Advisors, LLC (NY, NY 212-314-4600), member of FINRA, SIPC, and an agent who offers annuity and insurance products through AXA Network, LLC. AXA Network conducts business in CA as AXA Network Insurance Agency of California, LLC, in UT as AXA Network Insurance Agency of Utah, LLC, and in PR as AXA Network of Puerto Rico, Inc.

“One of the biggest challenges in selling financial services today is…”

All the noise surrounding the end client. My belief is that the typical client gets confused by the talking heads. They forget that the so-called advocates get paid by their sponsors and that their number one job is to keep their ratings up. If it’s on TV or the radio it has to be true!

Joe HolbergJoe Holberg


Joe Holberg is the CEO & Founder of Holberg Financial. The company is dedicated to educating and empowering millennials so they can achieve their financial goals and dreams. Previously he had a Fellowship at Google, taught middle school on the West Side of Chicago, and serves on many non-profit boards. He loves reading and learning.

“At Holberg Financial, I have identified two major challenges in selling financial services…”

First, it is hard to get buy-in from our target demographic: millennials. Millennials are brand-loyalists and skeptical of where to put their time, money, and dedication. Secondly, the financial industry is fraught with services and products that are pushed hard on millennials, so creating a service that seeks to empower and educate them, rather than capitalize on lack of understanding and selling products, is challenging (but worthwhile!). With 80 million millennials out there, we have our work cut out for us.

Harrine FreemanHarrine Freeman


Harrine Freeman is a financial expert, speaker and owner of H.E. Freeman Enterprises. She is the author of How to Get out of Debt: Get An “A” Credit Rating for Free. She is a regularly featured media expert and has made over 150 appearances including Market Watch, Forbes, and MSN Money.

“The biggest challenge in selling financial services is…”

Getting new clients. Finances are a sensitive topic and many people are terrified of examining their finances if they are not where they want to be or have not achieved the financial goals they desire. Many are also still leery of financial professionals due to the mortgage crisis in 2008. Everyone wants to give the impression they are doing better than they really are and are in denial about their true financial picture, resulting in a paralyzing fear of the unknown.

You can overcome this by reaching out to your social circle of friends, co-workers, relatives, and neighbors to ask for referrals. Create a referral program and share with your social circle. Offer to pay a fee for referrals to maintain a constant flow of new clients.

Partner with organizations and affiliates to reach new audiences to get prospect clients.

Jamilah McCluneyJamilah McCluney


Jamilah N. McCluney is principal and senior adviser of MoneyMD. She implements strategies for those misinformed by poor and outdated financial advice or those who have been overlooked due to a lack of large finances or wealth. She believes you have to start somewhere and is interested in helping you start right where you are.

“One of the major difficulties with selling financial services lies in…”

Trying to reach someone who does not know they have a problem or that they necessarily need you and your expertise. Finances happen to be one of those avoidable situations that most people would rather push to the back of their minds. I liken it to the profession of a doctor. Usually, people will only go to the doctor when something is wrong. Not just wrong, but no longer avoidable: I’ve had this problem for ages, Google can’t fix it, and my best friend didn’t have the answer.

Imagine exposing your deepest fears and inadequacies to someone you may not know very well. Admitting your financial ignorance out loud not only vocalizes it to someone else, but forces you, the financial ignorant, to face the actual truths and realities of where you are, what you don’t know, and where you need to be. My financial practice happens to work exclusively with healthcare professionals. What I’ve found is that there is an overall sense of pressure and expectation for the “doctor lifestyle”.

People assume the profession’s salary (not taking into consideration student loans and other debts of course), and expect you as the doctor to drive a certain luxury vehicle or to live in an upscale neighborhood while shopping and dining with celebrities. Under this pressure, many try to live the lifestyle and keep up with the expectations while overextending themselves tremendously. Some people would rather keep up with the image and façade and stay where their ignorance appears as bliss which also makes it challenging to shake up someone’s fantasy world.

Over time, the distrust for financial professionals has increased. From the Bernie Madoff-types and the “American Greed” marathons to the daily newspaper stories, those being misguided and deceived are magnified. Think about it. You rarely hear stories of a financial advisor guiding his/her clients to financial freedom. That’s not that exciting and engaging for news purposes. But you will hear about the latest financial Ponzi scheme or someone’s little old grandmother being milked out of her life’s savings.

There is so much varying financial information that prospective clients become confused as they are being bombarded with conflicting financial information and recommendations. Building trust is something that takes time and is not easily done over the phone or a one-time meeting, so being able to earn that trust and really be embraced with someone’s financial future is challenging.

All in all, I believe most of the challenges presented to those selling financial services can be eliminated and overcome. People are looking for someone relatable, someone who understands his or her financial struggles and who does not come from a place of judgment or ridicule. Deep down, once the person is really open for change, having a warm, compassionate person who truly cares about their money and future will shine through and slowly but surely overcome their resistance.

Brandon HowardBrandon Howard


Brandon Howard is a web designer, marketer, problem solver, and most importantly an entrepreneur. He owns several online businesses providing a wide range of products and services in different industries, both nationally and internationally. Brandon strives to find unique ways to help small businesses.

“The biggest challenge we face in selling financial services online is…”

Gaining the trust of potential leads. It is imperative that the website is high quality, very informative, and includes an easy and risk free way for visitors to contact a financial service representative for more details.

Marc ProsserMarc Prosser


Marc Prosser is the co-founder and managing partner of Marc Waring Ventures, a firm which develops specialty internet properties for high value audiences. The company’s portfolio of websites includes Fit Small Business, which provides product and service reviews for small business owners. Prior to starting Fit Small Business, Marc was the CMO of FXCM for ten years. He joined as FXCM’s first employee and grew the company to more than 700 employees.

“I’ve been involved in financial services marketing for 20 years now, and in that period, the biggest challenge has remained the same…”

Almost always, the biggest obstacle in winning a customer is establishing trust. Why should clients trust that you are telling the truth and that you have their best interests in mind? These days, there’s also a growing trust
issue at stake: can you keep their data safe? In financial services, you’re often trusted with the most sensitive data someone has. And every time they work with a financial services firm, there’s a chance of that data getting stolen or becoming public.

And trust isn’t easy to establish. Telling someone to trust you is rarely effective. There’s no one thing you can do. Trust is built into your marketing, your sales methods, the delivery of your services, what other people say about you, and a number of other factors, most of them intangible. You can’t just run a marketing campaign and resolve that obstacle.

Michael EcksteinMichael Eckstein


Michael Eckstein is a tax accountant in Huntington, NY. He provides straightforward and painless tax services. Eckstein is trying to break the decades-old stereotypes and make a trip to the accountant a pleasant experience.

“My biggest challenge in selling financial services is two fold…”

On one hand, my services aren’t glamorous and, on the other, I’m not a salesman by any stretch of the imagination.

I’m a tax accountant. I prepare taxes, keep records, and consult. These aren’t glamorous services. I don’t help people make money. I help them save it. It’s a hard angle to pitch. No one wants to pay money just to save.

On top of that, I’ve never considered myself a salesman. I know the days of not selling yourself are long gone. But, that’s not the type of business I want to run. I want my clients to know that I keep their best interests in mind and that I don’t see them as walking piggy banks.

So, I find myself between a rock and a hard place. I either pitch hard to overcome the banality of my services or continue down my current path. For now, I’ll stay steady on my course.

Priyanka PrakashPriyanka Prakash


Priyanka Prakash is a finance specialist at FitBiz Loans, an online platform that brings together all of the major financing options to help entrepreneurs and business owners get low-rate business loans. A former startup attorney, Priyanka now focuses on helping small businesses understand a variety of financial topics, such as credit scores and loan rates. Her work has appeared in Fit Small Business, Credit Karma, Go Banking Rates, The Motley Fool, Business Journals, and other top publications.

“The biggest challenge in selling financial services to clients is…”

Finding a way to clearly communicate the type of financial services you are offering, as well as the people whom it will serve. Financial services, loans in particular, used to be pretty straightforward. A mortgage was a mortgage, a student loan was a student loan, and a business loan was a business loan. For most types of loans, you simply walked into your local bank and if your application was decent, you qualified for the loan.

The FinTech revolution has completely changed how people get loans and where people go to get loans. For example, an individual who is starting a business is probably overwhelmed by the sheer number of options. He or she can go to a crowdfunding platform like Kickstarter, get a personal loan from Prosper or Lending Club and use it to start the business, or get a short-term business loan from OnDeck or Kabbage. Where the person goes will impact the price they pay, how long they’re in debt for, and how much money they can borrow.

That’s why it is critical for financial services firms to clearly communicate who their target customer is and the value adds that they offer. Is your company making it easier for people to get a loan? Faster? Are you appealing to a group that’s traditionally been underserved by banks? You need to make these things very clear in your marketing and sales

Jeff JonesJeff Jones

Jeff Jones is a CERTIFIED FINANCIAL PLANNER and member of the financial planning team at Longview Financial Advisors in Huntsville, Alabama. He is a graduate of the University of Alabama Huntsville with a Bachelor of Science in Information Technology and of the University of Alabama with a Masters in Financial Planning and Counseling.

Longview Financial Advisors, Inc. is a fee-only, fiduciary Registered Investment Advisor (RIA) firm working with clients throughout the Southeast with offices based in Huntsville and Gadsden, Alabama. They provide comprehensive financial planning and wealth management services to philanthropic professionals and retirees.

“When most consumers think of financial advisors, they often envision…”

An investment advisor buying, selling, and trading for them in an investment account. For advisors who identify themselves as financial planners, it can be difficult educating consumers on the difference in the service offerings. We believe that great value lies within a goals-based financial planning process where investment management is just one piece of a larger puzzle. Financial planning is where client goals are identified and married, not just to a retirement plan but also to the other disciplines of their financial plan: cash flow, estate, education, charitable and philanthropic, investment, insurance and risk, and tax planning.

Because the financial planning industry is still fairly young, it’s difficult for consumers to determine the value and thus the cost of such a service. It’s easier to understand paying fees and commissions to investment brokers because that service model has existed for so long. For most of our clients who have walked through and continue with the financial planning process, they have found where the value lies.

Grafton RobinsonGrafton Robinson


Grafton Robinson manages digital marketing efforts at Insureon, the fastest-growing insurance firm in the country. Insureon is an online-only platform that generates B2B retail leads through its search presence, affiliate relationships, and digital outreach.

“For us, the biggest challenge in selling financial services to clients is…”

Maintaining a balance between being data-driven company and one that continues to offer our customers a friendly, personal experience. And data helps us do that too.

For us, the term ‘analytics’ really just means ‘customer experience.’ We look at data to see what exactly our customers want and what they respond to – then we adjust our approach.

We work with small businesses and help them find insurance. That means our customers are a lot of first-time business owners and people who are making the leap to launch a new enterprise. So what does our data tell us about them? When you’re first hanging up your shingle, you’re worried about how much everything is going to cost. We found that in both our 1-on-1 customer interactions and in the huge amount of data we’ve collected from surveys and web analytics.

Because of this, we decided to do something unconventional in the FinTech world. We publish reports about the cost of insurance and make as much of our cost data public as we can. Usually, that stuff is kept under lock and key. But we’ve found our customers respond to this transparency, and that’s an insight that was driven home by the data we’ve aggregated.

Going forward, we have to be agile, ready to adjust to what our customers want. We keep our ears open to the customer, and we do that through data and through our 1-on-1 conversations with them. That challenge is certainly difficult, but that’s also what makes it rewarding.

RJ IrvingRJ Irving


RJ Irving is a former Morgan Stanley advisor and the co-creator of Melius, which offers people a financial education in a language they can understand and delivers the simple steps people can take to deliver the biggest impact on their financial future through simple financial reports and guidance.

“The number one challenge in selling financial services to clients is…”

To NOT sell them. People do not want to be sold, but they welcome a professional guide along their journey. The entire U.S. workforce is the most educated group of people we have ever seen and they want to self-discover and understand the true benefits of everything they purchase. They then want a professional to help them find the best product in the marketplace for their specific needs.

John VespasianJohn Vespasian


John Vespasian is the author of seven books about rational living, including When everything fails, try this, (2009), Rationality is the way to happiness (2009), The philosophy of builders: How to build a great future with the pieces from your past (2010), The 10 principles of rational living (2012), Rational living, rational working: How to make winning moves when things are falling apart (2013), Consistency: The key to permanent stress relief (2014), and On becoming unbreakable: How normal people become extraordinarily self-confident (2015).

“The top 3 challenges in financial services sales include…”

1. Deluding yourself with predictive statistics.

Too many sales are lost because salespeople do not bother to follow up on prospects that do not fit their ideal customer profile. This is a major mistake. If someone shows interest in your financial services (insurance, mortgages, etc.), you should follow up properly on that lead, even if the person looks too young, too old, too poor, or too whatever. A good salesman should follow up on every lead and try to close every sale. Do not rely too much on predictive statistics about a mythical ideal customer. Customers are defined by their buying behavior, not by their demographic profile.

2. Failing to use your time productively.

A good salesperson does not have downtime. He does not have any moment of his working day when he is not directly or indirectly trying to close a sale, making a sales presentation, or following up on a sales lead. Working time is working time. Use it wisely to maximize your results, and do not waste a minute on empty talk, braggadocio, and gathering useless information. It is up to you to reduce your unproductive time to a minimum, preferably to zero.

3. Comparing yourself with other salespeople.

More often than not, comparisons tend to be psychologically destructive. Each individual has different background, experience, and motivation, and it does not make any sense to undermine your self-confidence by comparing yourself constantly with salespeople that are more successful than you are. Instead, you should try to learn as much as you can and see how you can improve your sales performance. The best approach is to compare your achievements today with the greater achievements that you expect to attain in the future.

Eric M. JacksonEric M. Jackson


Eric M. Jackson is the CEO and Co-Founder of CapLinked, an application for secure enterprise sharing. He previously served as PayPal’s first head of U.S. marketing and is the author of The PayPal Wars.

“The biggest challenge financial services representatives face when selling financial services to clients today is…”

Security. Clients in financial services have greater security concerns than those in most other verticals because of the sensitivity of the data they’re working with and the frequent need to share information with outside parties. Add to this extensive regulatory compliance needs, and you can see why security is at the forefront of financial service firms’ minds when choosing a new product. This is why FinServe firms so often continue to rely on old and outdated software – it’s viewed as well-known and therefore safe, even though antiquated technology can pose a host of other risks.

There’s no one silver bullet for addressing these concerns. At CapLinked, we’ve incorporated best practices into our product and our company’s procedures, and we’ve completed third-party audits to document this for clients. Since we sell enterprise sharing software that’s designed to keep data safe when it’s shared with outside parties, it’s crucial that clients understand the extent to which we go to embed security every step of the way.

Mike ScanlinMike Scanlin


Mike Scanlin is the CEO of Born To Sell, a web site dedicated to self-directed covered call investors. He has been trading covered calls for 35 years.

“The biggest challenges we face when selling financials services are…”

The high cost of sales and giving each customer a personalized view of our offer.

Many advertisers are trying to reach the same desirable customer set: people who have money and need financial services. If you use PPC ads to attract new clients, the financial services keywords are among some of the highest bids. You might pay $10/click for some investment-related words. With a 1% conversion rate the customer acquisition cost would be $1000. Quite high.

The second challenge is making each person feel like our services are catered to their personal needs and situation. Everyone has a different financial situation, set of life circumstances, and risk/tolerance profile. Segmenting our offer 50 different ways to accommodate all clients is tough to do when marketing or advertising. Yet, customers want to know that they’re getting individualized treatment, and not just one-size-fits-all type solutions.

Patrick PearsonPatrick Pearson


Patrick Pearson began his career with, Burson-Marsteller, the world’s largest public relations firm. He parlayed the training he received from renowned PR practitioners, to a marketing career that has spanned nearly thirty years. Among the highlights include a tenure as the director of marketing for Hersheypark(tm). Pearson currently serves as the director of marketing for Chrome Capital, a provider of consumer leases of pre-owned Harley-Davidson® and new Indian® Motorcycles.

“The single biggest challenge we face in selling our financial services is…”

Relying on our dealer partners to represent our products. Its akin to sending your children off to college and hoping they make good decisions. You want to be there, looking over their shoulders and telling them what to say and do, but that is not a viable option. We have overcome this obstacle by doing a few things that generally come down to providing marketing support to dealers. We provide them with tools that make it easy for them to explain how a motorcycle lease works. Chrome Capital also has a full-time director of training and a team of field sales professional who regularly visit dealers. We compete with banks and other financial institutions jockeying for a share of the V-twin, American-made motorcycle market (Harley-Davidson® and Indian® Motorcycles). Some dealer partners have fully embraced leasing to the point of exclusively recommending to riders.

Tammy JohnstonTammy Johnston


Tammy started working in the Financial Services Industry in 1993. The first 9 years of her career were spent working in regional offices, for independent agents, and as Brokerage Manager for two different MGAs. Determined to be more than just another insurance salesman, Tammy founded The Financial Guides. She set about working with clients in a totally different fashion.  Feeling that everyone needs a sound financial education she created her first class “Financial Journeys.” The goal was to provide the accurate, unbiased, basic information in simple English that we all require, but can’t easily find.

“The biggest challenge in selling financial services is…”

Making the client comfortable enough to get ‘financially naked.’ In order to do my job properly and actually help the client I NEED TO KNOW EVERYTHING. All the dark, dirty secrets. Everything they are embarrassed about or afraid of. What are their goals? How do they actually handle their money and make their decisions in real life (not what they want the world to think)? Once the trust is built up and they reveal the truth, putting together a plan is a cake walk.

Kayla EthanKayla Ethan

Kayla Ethan works for RebatesZone.

“One of the biggest challenges in selling financial services to clients is that…”

The financial services sector has some of the biggest scams in history, so trust is very difficult to gain, especially in stock brokerage. But, this has had a mixed effect on the general potential customer base. High net worth individuals are more likely to do the proper research and so is the case with people investing out of their retirement savings. This favors financial advisors like us, who are not out to scam people.

The biggest challenge, however, is managing expectations, while still educating newcomers about the steps that they will be taking in near future. There is this absolute haste to get the maximum gains, but stock market gives the biggest rewards to those who take risks. You just cannot promise large returns if the person on the other side is not ready to take some risk, and the thing about risk is, well, it is risk. How do you counter it? Sell a solution, not your service. Most people are not interested in the technical jargon anyway. Understand why the person wants to invest and choose a course from there. For example, if it is a small company which wants to invest surplus cash until their next payment, recommend a safer, short term investment, etc. The main point is that acquiring customers and then keeping them is the real deal and you cannot retain clients by misguiding or making false claims. It all comes down to building trust and managing expectations in the end.

Peter LeedsPeter Leeds


Peter Leeds is the author of Penny Stocks for Dummies and Invest in Penny Stocks. Along with his full team, they publish Peter Leeds Stock Picks, a newsletter which focuses on speculative shares.

“The biggest challenge most financial services sales reps face in selling financial services to clients is…”

Most people know just enough to get themselves into trouble. This is no different with the financial service industry, and potential customers often fall prey to confirmation bias, whereby they see what they want to see.

A single argument, no matter how flimsy, might get their attention, and they will act as though their position is correct. This results in them ignoring counter-points, while focusing on (and even seeking out) any data which supports their position.

Unfortunately, they are only correct about 50% of the time, and their approach can lead to some significant losses.

In addition, this same situation plays out whenever the individuals are getting caught up in an investor mania or stampede. When Bitcoin is all over the news, or marijuana penny stocks, or dot com companies, they will ignore incredibly weak financial positions just to take a gamble on the latest hot and impossibly over-priced investments. Any opinions that don’t suggest they jump on board the latest craze are discounted.

Richard ZeitzRichard Zeitz


Richard Zeitz is the President of Bravias Financial, an independent financial advisory firm. He has worked in the financial services industry for 20+ years and has extensive knowledge in retirement planning, investment management and insurance planning. He specializes in developing financial strategies that help clients create a reliable income stream they can’t outlive, while working towards growing and protecting their investment portfolios along the way.

“When I think about my career in financial services, and the biggest challenges I have day in and day out when it comes to selling financial services, I always come back to…”

Being an independent advisory firm. Running my business without the support of a larger firm is a decision I made awhile back. After years in the corporate world I made the choice to be independent because I didn’t want to be captive to selling financial solutions that were proprietary. I wanted to wake up every day and do what I felt to be best for the client, not for the firm.

Obviously, being an independent advisory firm certainly has its benefits, but the challenges are there as well. At the forefront, its always about name recognition and branding, and everything stems from me being given the opportunity to explain who we are, what we do, and why working with an independent financial advisory firm is a plus. FAs at the bigger firms don’t have to overcome this hurdle, but I do, often. There are many big brokerage firms and wire houses that have spent many years and big budgets on building their brand equity. These are the household names everyone knows and trusts, and they are everywhere you turn. Most consumers flat out trust these names and this is the first place they often turn to get their investment advice. A challenge I have most days is explain to the prospect the difference between them and Bravias Financial. Bravias is not a name they have heard of (in most cases) and we don’t spend millions a year on advertising. We just don’t have that brand they can associate with. So, naturally I have to spend some time explaining to them the benefits of us being an independent firm.

Just as a consumer has the freedom to choose a financial advisory firm they believe is best suited for their needs, we have the freedom to choose from a greater depth of investment services and products. I have the flexibility to customize solutions for clients by choosing products from a broader array of options. We are not owned by a bank, brokerage firm or insurance company, and this way we are able to work in a conflict-free environment and act more as a fiduciary by putting the clients needs first. Also, at many national firms, there are account size minimums, sales goals, etc. As an independent advisory firm, we have the ability to work with whomever we want (regardless of account size), and we aren’t under the pressure to hit certain sales numbers to satisfy management.

Holmes OsborneHolmes Osborne


Holmes Osborne is the Principal at Osborne Global Investors.

“The single largest challenge in selling financial services is that…”

There are no barriers to entry for a financial advisor. You don’t even need a high school degree, just whatever securities license. A hair stylist has to have more training (by law) than a financial advisor.

There are too many people with securities licenses out there. Insurance agents, stock brokers, money managers, and financial planners.

Andy BranterAndy Branter


Andy Brantner is a CFP® who owns StartInvestingOnline.com, a site which seeks to help new investors get the ball rolling with low-fee, easily-accessible online investment tools.

“I think one of the biggest challenges these days is the fact that…”

There are now so many legitimate do-it-yourself investment options available online. For many first-time investors, robo-advisors like Betterment offer an easy pathway to get started with a low-risk portfolio at a very low fee (ranging from .15%-.35%). While these automated investment services might not be right for every single investor, they drive a hard bargain and do well for many.

Justin GoodbreadJustin Goodbread


Justin Goodbread, CFP®, is an entrepreneur and a family man as well as an outstanding financial planner. He started his first business at 16, a landscaping business that grew into a partnership.

In 2009 Justin founded Heritage Investors, where he helps individuals, businesses, and nonprofits attain their financial goals. Besides being a CERTIFIED FINANCIAL PLANNER™, Justin holds Series 7 and Series 66 licenses, qualifying him as a securities agent and an investment advisor representative. He holds an associate’s degree in horticulture from Abraham Baldwin Agricultural College and a bachelor’s degree in business management from the University of Phoenix.

“When it comes to the challenges faced by financial services representatives in selling services to clients…”

The problem is the word selling! People do not want to be sold. They want to be guided and taught. The problem is that we are accustomed to purchasing things on an ‘as needed’ basis and in the financial world, this system leads to a mess of a financial plan. Once a client understands their specific goals and how the products or services help them obtain their goals, then and only then are they willing to implement the products or services of the financial world.

Mitchell SouzaMitchell Souza


Mitchell Souza is the Director of Sales at Capital Retail Solutions, Inc., a financial service software distribution/sales/marketing company. Souza has been in sales his entire life and with Capital Retail Solutions for the past 5 years. His focus is put into developing the company’s sales team and expanding its national footprint through direct sales and partnerships. The company’s different software  programs allow Financial Service Centers to provide money services to customers, for example cashing a check, paying a bill, transferring money, etc.

“There are a few key challenges in financial services sales, including…”

Learning Curve

Being that our sales type is considered Business to Business (B2B), it’s our job to educate and qualify the merchant on the necessity for a specific type of bank account, enabling them to perform these money services. Unless they already have an account, they are directed towards Capital Compliance Experts, a division of Capital Retail Solutions which specializes in compliance consulting, banking, and audit preparation and assistance. This can typically add weeks to the sales cycle and can be an overall deterrent for the merchant even getting into the business!


Simply put, money tends to be one of the most sensitive subjects in people’s lives. It can surface more anxiety and fear than many other areas of life. With that being said, working with merchants specifically, it’s your job to earn their trust. If the merchant doesn’t have confidence in you as a salesman, they will move on. They need to understand that you have their best interests in mind, always.


Specifically in the financial service industry, there are definitely risks involved. In many scenarios, merchants are providing funds to consumers prior to them actually being verified and available. This leaves the merchant at risk for serious financial fraud, sometimes in the thousands. Not every merchant is aware of risks, so that alone can be a big obstacle.


Upfront cost is never easy to swallow, which is why virtually everything can be financed nowadays. What many store/business owners don’t understand is that there is a cost in doing business. Haven’t you ever heard the phrase, if it was easy, everyone would do it? Well this truly applies to consumers, as well as business owners. Our job is to help merchants understand how to use our software to mitigate fraud and improve their business. If done right, there will be a 100% ROI in just the first few months!


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