To Succeed in Sales…You Have to Fail

SDR Insider #5

It can be difficult to tune out the rest of the world and succeed in sales, especially during times like these when layoffs are all around us. So, what advice could someone who has continued with their sales career after a round of layoffs share with current SDRs?

The answer: a lot.

And that is exactly what we took away from this interview with former dD SDR Darcy Clew – a lot of advice and motivation to continue working towards your goals, even when the path to get there may seem treacherous.

The ideas behind the topics and questions in Episode 5 of the SDR Insider started with a quote from Darcy: “To succeed in sales…you have to fail.” This quote has become the episode’s title.

Darcy addressed this idea at various points throughout this episode, which also ties into the lessons of Episode 4: ‘No’ in Sales Isn’t Rejection, but Redirection.

Episode 5 takes the conversation a step further while inspiring others to keep trying.

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Key Takeaways

What Next?

A time of flux or change often forces us to examine ourselves from different perspectives. That is exactly what happened to Darcy after she experienced her first layoff.

After some time and soul-searching, Darcy remembers thinking to herself, “Sales is…who I am.” And she has continued to thrive in the sales world ever since.

“I am constantly going out and making friends, marketing myself, or networking. It is really hard to find a position that allows me to have that side of my personality shine the same way a sales role does.”

When it came to her next move, she considered the things she liked and what she wanted in her next role, which confirmed her interest in furthering her sales career.

“There is a certain breed of person who becomes a salesperson, and I like being around those people—the ones who are hungry and driven.”


Success and Failure Are a Package Deal

Despite popular belief, success and failure are not separate entities but a package deal. “A lot of learning and growth (in) sales comes by doing things wrong.”

Darcy’s advice for beating rejection? Is “learning how to navigate around that rejection in a way that’s positive and conducive to your learning, as opposed to… retreating internally”

Turning the bad parts of life into learning lessons is not only a golden rule for business and sales but also everything else.


Work On The Things You Find Difficult

Speaking of turning negatives into positives, Darcy shared in this episode how she took things she had previously found difficult to now being assets to her career.

For example, she started asking herself, “How am I going to leverage data I am given on a daily basis….and see that data as something I can leverage to do better.” With this perspective shift, she saw not only direct translations of her work but also the money she was making.

Another example included taking a weakness and making it a strength, such as being more organized. This shift of perspective can be applied to anything in work or life you struggle with.


Attitude is Everything

Darcy’s final piece of advice on the topic? “A lot is about your attitude. A lot of it is about your mindset.”

“When something bad happens, I give myself 48 hours…after that 48 hours, it is time to get it back together”

Her checklist if you find yourself in a time of transition?

  1. Ask yourself, what are my transferable skills?
  2. Reach out to the network you have acquired and leverage it.
  3. Don’t be discriminatory in your job search.
  4. Be able to sell yourself and your resume.
  5. Have some confidence!

“The only time you really fail is when you stop trying”

💡 Editor’s Note: This episode is chock full of advice for an SDR hitting a rough patch – something that is inevitable in virtually anyone’s sales journey. In particular, her points on mindset and burnout are perpetually relevant.

We had Tad Bustin on our podcast to talk about the mindset required for SDR success – I recommend giving that a listen as a follow-up to this episode.

And we talked with Quinn Underwood about burnout prevention – another recommendation from me if you’re feeling like nothing is going your way and sales might not “be for you.”

Sales is a grind – no doubt about it. But without the right attitude, it can become unbearable. Darcy’s story and advice is a great reminder of that and a valuable listen for SDRs new and old.

Sales Rep new or old, we hope you found this episode and post helpful. We are looking forward to sharing more insights from top performers through the SDR Insider, a new monthly initiative from demandDrive.

If you are interested in being included in a future episode or have an idea for a conversation, feel free to reach out to Madi at

(00:00) [Music] hi everyone and welcome back to SDR Insider insights from Top performers I’m very excited today to be talking to Darcy clue um she is a former demand Drive colleague of mine and we’re excited to talk about the success versus failure in sales today and I think this is a great episode to start the new year
(00:27) off with so hi Darcy and welcome to the podcast how are you good Maddie I’m good thanks for having me really excited to get into it course I know I’m really excited too um so a little bit of background for anyone who’s listening who is either new to the company or didn’t have a chance to meet you or is listening from somewhere else
(00:49) that isn’t demand drive centrick at all um tell me about your road to getting into the sales world what was that like um specifically the SDR role that you started in yeah so I think um you know I initially gravitated towards sales just after you know kind of growing up and being a really extroverted outgoing
(01:14) person you know I was constantly you know recommending things to my friends and my family and so one day I think my dad said something along the lines of I always knew you were going to be in sales or something silly like like that and so I was like well okay you know I’ll I’ll think about it I don’t know um
(01:33) and then when I graduated college I actually started just looking into it more and I was like okay well what can I do with a political science degree you know like I really didn’t want to go into politics specifically and so I was like well politics was really networking and it was really learning how to
(01:51) navigate different personalities and and be able to advocate for different things and so I think that’s how I initially got into sales with that said I think a lot of my background came from retail like I I worked at a at a mall selling like women’s apparel for a little bit um and So eventually I just realized I
(02:12) needed to kind of put together some more experience and kind of fill out my resume a little bit more and learn how to Market different products that weren’t just shoes or um shoes or a dress that was in a retail Mall yeah I always asking that question sorry I didn’t mean to cut you off I was just saying I always love asking that
(02:37) question because it’s really everyone has different everyone’s different answers and also I’ve heard a lot of like retail and also food and Bev backgrounds which I feel like is some I did both too in college so I think it’s just interesting to kind of hear everyone’s backstories and how how did they wind up in their
(02:58) first sales job and um yeah I think I think it’s just fun to to hear but I didn’t want to cut you off what else were you saying about it fine I um no I think so my biggest or the closest thing that I would have had to before demand Drive was actually working at a call center doing surveys and so I was calling people and asking
(03:22) them about their political beliefs and how much money they made a year and doing like census work essent and you know there’s nothing worse than selling something to someone other than having to call them and be like how much money do you make and how are you gonna vot this year yeah and they’re like is
(03:39) this and I was like okay well if I can do that the odds of anything else being significantly harder than that is pretty slim and so when I started looking for jobs demand Drive kind of stuck out because I was like okay it’s not a specific prod it’s a variety of different clients and so when I ended up
(04:01) at demand Drive I was on a number of different projects one of which was financially based um another of which was law based and like law Tech um so I it was like a recording device for lawyers so that’s um that’s kind of why I gravitated towards it I just wanted really well-rounded experience in terms
(04:23) of selling different things and being able to talk to different groups of people so yeah no that’s super interesting yeah no it’s interesting to hear and hearing that you did the survey work before I’m sure that this felt like a walk in the park compared I mean there’s obviously things in sales that
(04:41) are difficult too but I’m sure that it it felt a lot easier compared to that because I’m sure people just do not want to talk to you yeah just don’t scare me anymore yes cannot cost be worse than someone from Northern New was like I wrot my guns know yeah so so it was a really good experience kind of being able to to work
(05:09) at demand drive and get like all of the different experience with people that were selling different things and you know networking with different clients that were also you know just working in completely different Industries and so I think that gave me a really good kind of foundational understanding of sales in
(05:26) the broader industry and the field um and so I thought it was really valuable to work there for as long as I did that’s awesome and I did want to ask so did you ever I know there was a time where you weren’t at demand Drive anymore and it was kind of a flux period and I’m curious did you consider shifting away from sales at any point to
(05:49) another industry or did you know I’m going to stay in sales like this is really something that I eny enjoy doing and I I want to continue the process and what made you eventually stay I think would be interesting to hear and probably helpful to some people who might be in similar positions yeah I um so it’s funny when
(06:12) when I left or when I was laid off at demand drive and my projects ended you know it was definitely like a really weird time for me where I was like oh well like you know if these projects ended like it must have been because I didn’t sell them well enough or or the like I wasn’t able to Market it well
(06:32) enough and so like it’s really easy kind of sit in those feelings of oh I didn’t do something well enough and so I definitely gave myself a little bit of time to feel that way which I think it’s entirely reasonable you know like um but towards the end I was like wait but like sales is kind of who I am like I’m
(06:52) constantly going out and making friends or marketing myself or networking and I think you know it’s it’s really hard to to find a position that allows me to kind of have that side of my personality Shine the same way that a sales role does you know and being able to kind of apply those skills that I’d gotten at
(07:15) demand drive to something else I was like okay well they’re super transferable I definitely poked around in a number of different fields and different Industries and when it came down to it I was like okay well what are the things I really liked and you know what like in terms of looking for the next role what were the things that I
(07:35) wanted to find in it so a lot of them just were sales-based roles you know I liked the fastpaced I liked the competition of it I liked being able to interact with people on a daily basis be very client facing and so I think a lot of that you know ended me up in my next role which is also sales now um and in
(07:59) fact it’s it’s a similarish position to what I was doing at demand drive but it’s a little bit more tailored to my interests so you know I really liked finance and I really liked being able to interact with those clients specifically and so when I did find my current role obviously there were different things that I was looking for
(08:19) than when I had my first job out of college but the core beliefs of it were you know I wanted to be able to kind of be in a selling environment and I think like there’s a certain breed of person that becomes a salesperson and I liked being around those people you know like the ones that were just hungry and driven and you know
(08:40) really just wanted to like be powering through their day if that makes sense no that totally makes sense and as someone who also is kind of in a time of flux right now with projects I can definitely relate to that feeling I think think it can be very overwhelming and it’s something that we all experience at different points in our
(09:02) career paths especially in sales because it is so ever changing so just on that note um I would like to hear if you have any advice or any tips that helped you kind of change your perspective during that time um just to anyone else who might be dealing with something similar or maybe in the future or have in the
(09:24) past that kind of helped you change your your perspective Ive in your mindset I’m curious if you have any tips yeah um I I think I have a lot you know I love being able to teach people things um but that that’s also a sales thing but I think you know in general right you know one of the things I said
(09:44) to you before we even hoed on this call was you know if you haven’t failed in sales you also probably haven’t succeeded because I think a lot of learning and a lot of growth in sales comes from doing things wrong you know like doing it wrong the first time or not succeeding at the goal and finding kind of the the power and drive to go
(10:07) give it a try again I think you know um when I was searching for kind of the current role that I was in I i’ really evaluated kind of what I wanted to be measured on and I determined I didn’t necessarily hate that I was being measured on like meetings booked or you know um how many clients signed on but
(10:32) what I really wanted to find was somewhere that I was empowered to fail and try again and finding teams and surrounding yourself with people that Inspire that in you I think was super important and so that’s definitely something I recommend to anyone who’s looking into sales and making sure that they are really getting a good sense the
(10:56) team and the culture because I think that makes a huge difference um second I think being able to kind of take the rejection that you get in sales and turn it into something positive right like it’s such a rejection heavy position and such a rejection heavy job in general that you have to have a bit of a thick
(11:18) skin but I think it also is like learning how to navigate around that rejection in a way that’s positive and conducive to learning as opposed to kind of retreating internally and you know really faulting yourself for it it’s like you can fault yourself for it as much as you want but eventually like you
(11:36) have to be able to turn it around and that’s what sales is it’s like getting rejection or getting objections and being able to turn it around and make it something that’s positive for the person you’re talking to including yourself does that make sense that’s amazing advice like really amazing advice and I think um I’m happy you
(11:57) brought up that quote because I was going to bring that up next because when you said that on our you know preall kind of just catching up since we hadn’t talked in a while you said that quote and it really stuck out to me and it really was what I wanted to base the questions for this episode off off of
(12:14) because I think it is so profound to say you know you can’t have success without failure it is they come together it’s a package deal and so I would love to hear like do you have any quote unquote like someone else would see it as a failure in your sales experience that has actually given you um success and in the
(12:39) long run because it’s taught you something I’m sure you have plenty of stories but um because I know I do but is there anyone that kind of sticks out to you that you know was something that maybe looks like a failure but it ended up being something that really ultimately made you successful I mean I think there’s so
(13:01) many things that I have you know made mistakes on or failed at over the course of just not sales like like there are so many things that have that I’ve done wrong or I could have done better at at any given point in time that ultimately kind of framed my perspective moving forward and I think um you know especially when I
(13:23) got laid off at demand drive and a lot of those feelings of like you know I didn’t hit my quota or I didn’t hit my numbers you know for a certain period of time or I didn’t do something enough um you know I I kind of took that on board and there were certain things where it was like you know maybe I
(13:43) wasn’t as prepared when I was making these calls or maybe I didn’t put in the actual initial groundwork to really understand the product and the pain that people that I was selling to were experiencing and so when I like obviously got into a new role and you know I’m very happy in it I’ve been here for a little over a
(14:04) year now um I brought a lot of that on board with me where it was like okay well how am I going to kind of Leverage the data I’m given on a daily basis whether that was number of calls um to meetings booked Ratio or you know stuff like how to phrase an email and what generated opens like learning to kind of
(14:25) see that data as something that I could leverage and learn to really use in my day-to-day to help me do better was was a very big change from kind of seeing it as oh I have to make 50 calls today or my manager is going to be upset it’s like no I have to rip 50 calls right now because I plan to make a bunch of money
(14:48) because of it you know um and I want there to be like kind of those direct translations of the work I was putting in to the amount of money I was making and so I think overall just learning to kind of Leverage the things that definitely got me down previously you know especially just seeing like quantitative analysis of what I was
(15:10) doing on a day-to-day basis and what wasn’t working was like okay well how do I take this data change something and then generate more revenue or more calls or just more meaningful interactions with prospects in general I think that made a huge difference and um that and also I think like organizing you know
(15:32) like I used to think sales was like kind of easy you know especially when you’re the type of person who just goes out and talks to absolutely everybody um you know it was like H well sales should be super easy um and I think it was it was really like naive to say that or think that way when I I really didn’t understand the
(15:54) products I was selling and I didn’t understand the prospects I was selling to and what the pain was and so learning to kind of organize my day in a way that allowed me to be really prepared to rip something like 50 calls or 50 emails every day and actually knowing the prospects I was reaching out to I think
(16:11) that ended up just generating a lot more success on my end does that all make sense no no it does and I appreciate you sharing that because I think a lot of times no it’s a great answer and I think a lot of times we it’s hard to kind of look back on things that maybe we didn’t do so well and say okay this can be a
(16:32) learning lesson but I think if you’re able to do that you’re obviously a very strong person a strong salesperson to be able to use that to make you better and I think not everyone can do that so it’s really good advice for people to hear and listen to because it’s it’s very unique not everyone is able to do that
(16:52) so I hope you know that listening to that as well um but I I would like to ask this just because I know so many people are experiencing this right now and you talked about you know being laid off in that time period And if you have any advice for anyone who is experiencing that I know like tech industry a lot of
(17:14) that is happening right now I mean layoffs happen all the time they happen all the time but I I do know I feel like I’ve seen an influx of people experiencing it right now so if there’s any advice you can give What would you say to anyone who is either recently laid off or maybe in a time between jobs
(17:31) or projects or whatever it might be um what would your advice be to that person or maybe like look back to yourself and what advice you would have liked to hear or something like that yeah um I you know I think one of the best things that that I can really impart to someone who’s kind of in between jobs or is really kind of in
(17:55) that that flex period is a lot of it is about your attitude you know a lot of it’s about kind of your mindset when that happens and like you my thing is like when something bad happens or i f something up I paron my French but um I give myself like I give myself like 48 hours right I get 48 hours to wall in
(18:18) self-pity if I want or you know just really be like screw this I don’t want to do it anymore like I hate it I hate it but after that 48 hours right like it’s time to just start getting it back together it’s like okay I can fall apart but like now let me like gather all of my things and like start kind of looking
(18:37) at what I’m working with you know um and I think the first thing you have to kind of evaluate is what are my transferable skills you know what do these lend themselves to what are the different rules that that these can be applied to really easily so that would I I would say is the first um and two I think you know one of
(18:55) the things that I I kind of took from one of my co-workers Grace um was you know really reaching out to kind of your network that you’ve acquired over the years and and just kind of asking them what they’re doing or you know leveraging that Network in general to just better understand an industry or a
(19:20) job that you’re looking into and being able to kind of use those connections to either expand your horizons into a given industry or or even ultimately like maybe get a job or you know whatnot so your network is super important so that I would say is step two and then step three is don’t be so discriminatory in
(19:42) your job search you know um I think one of the things about sales is it’s a bit of a volume game right and regardless of what you’re selling whether that’s your resume or that’s a product um I think if you aren’t putting it in front of as many people as possible the odds of you getting bites on it are slim um and
(20:02) getting creative with that too I think is super important and so when I was interviewing I want to say I probably talked to something along the lines of 25 30 35 companies um and I wanted to take interviews with every single one I didn’t care what the job was I just needed to get back into the the flow of
(20:23) interviewing and talking to people again about myself because it’s when you’re in a job it’s like you’re not taking stock of all the different things that you’re doing and all the different skills that you’ve acquired but when you learn how to Market yourself to an interviewer I think it’s like if it’s the right role
(20:41) they’ll pick up on it but if it’s a role that you want and they aren’t sure then you need to be able to have those conversations and be able to articulate what you’ve done appropriately and based on a given role so even applying to some extent an inter interviewing for jobs is sales it’s just selling your resume and
(20:59) being like here’s what I bring to the table for your company and and also just having some confidence in that you know like if you are a really detail oriented worker or you you have a lot of energy and ambition to contribute to a role like note that and and take you know take stock of that and be aware of it
(21:20) and make sure that it’s conveyed over an interview and that way I think you will end up with roles that are much better suited to your personality and your workflow and the things that you’re successful at ultimately no that was great advice and I can guarantee that someone listening down the road either when this comes out
(21:41) or in the future is going to find that super helpful because like I said it’s something that I think is a little taboo to talk about no one really wants to talk about those weird periods of Life specifically in between roles or jobs or project or whatever it may be and so I think it’s great to give that advice and
(22:00) to share that and I know it’ll definitely help people um I would say that my main takeaway from this conversation and just chatting with you is the importance of failure and success I think sometimes we think that those two things are not connected but they are very much so and especially in sales you have to fail to succeed and honestly
(22:25) that’s probably going to be some type of the title in some sense because I think it’s just so great but I would love to hear from you just after talking um and all the different things we talked about uh what do you think would be like a main takeaway that you feel that you hope people listening hear from
(22:48) this yeah um so I think a couple things one is you know you know that phrase where it’s like you fall down seven times and you stand up eight um you know there is so much power in standing up that eighth time right and and being able to sit there and be like yeah well I’m trying again you know like um
(23:12) there’s a really good movie quote from like uh an Eddie Murphy movie that I really liked when I was younger and it’s like the only time he really fails when you stop trying and and it’s so cliche but it’s so true where it’s like you know if you give up yourself like if you give up on yourself like it’s it’s
(23:31) really hard to get other people to believe in you and so I think you know go in a little like delusionally confident um and like really believe in yourself and believe in what you’re doing for yourself and I think that goes a long way um and then second of all I think when you do find success I think
(23:53) it is so important to send the lad back down to other people who are struggling or want to get better and and really looking for those qualities of you know like hunger and ambition in other people in sales because I think it’s one of those jobs where if you don’t have people who are kind of championing you um whether
(24:16) that’s internally at a company or externally and your just general support system you know I’m going to shout out a couple people really quick but when I first joined my company there were two women on my team and it’s a very male dominated industry but or two wom ra Jon ring um and they both just like really
(24:36) took me under their wing when I first started and made sure that you know the the good qualities and the skills that I had not only didn’t go unnoticed but got channeled properly and so I think it’s really important especially as salespeople when it is such a competitive environment to really make sure that we are are pushing the people
(24:57) around us to be them their best selves as well and so I I got really lucky with it but but I think um you know it’s something to definitely take note of when you join a company is like you know what are the role models around you pushing you to do you know like who do you aspire to be or who do you expire or
(25:16) who inspires you around you and and finding that in a company is super important and so I think those are my takeaways it’s like when you fail stand up the eighth time and two when you do succeed make sure that you are pushing the people around you to succeed as well I think that’s super important especially in a role
(25:38) like sales no that’s so awesome and I I love that you brought up the two mentors specifically at your new company have been female because we talked about it a little bit and you know we don’t have to get into it too much but I do feel like sales is such a male dominated space so when you do find fellow saleswomen who
(26:00) you can chat with and talk about your experiences and I think you know you me and my friend Grace we definitely connected because we were three females starting off our sales careers and I think there’s there’s so much power in that and it’s really important as you move up the ladder to to um speak to people who are coming
(26:23) into their own too so that’s awesome yeah absolutely and also I just think talking about it with other women like you know it’s it’s almost a very different role as a woman too because like there are certain sales tact tactics that men use where it’s like if you go in super aggressive or or super you know like heavy-handed on prospects
(26:43) you know it doesn’t lend itself the same way if you’re a woman and so I think there are certain things where it’s like you have to learn from the other women around you how they’re finding success because I think you know it’s just not always the same for men and women in terms of how you Market something and
(27:00) how you’re perceived I completely agree and I think that’s why that really resonated with me like we both had the first part the same but I think the second part of just when you do find success to give back to other people but specifically if you’re a woman in sales like to continue helping other people who are starting um
(27:19) so I think that’s great and I really appreciate it I think this is a great conversation and I really appreciate your time and your openness and talking to everyone about your experience and I’m really excited for people’s listen so thank you yeah no I’m excited too and um you know anyone can reach out to me
(27:40) if they have questions obviously you know I um I love getting to catch up and talk about these things especially you know obviously with old colleagues but um yeah you know just in general I think it’s so great getting to talk with other people in sales or that are looking into it and just like hearing perspectives
(27:56) it’s awesome so what you guys are doing great that’s great yeah that’s oh thank you yes and I think that’s great for people to hear listening to like look up Darcy on LinkedIn if you have questions or if anything you want to talk about out to you she’s a great listening ear and has great advice as you surely saw
(28:16) during this episode so thank you for being here and we appreciate it yeah thanks for having me guys it’s been a pleasure